Sulfinamides as Highly Effective Amine Protecting Groups and Their Use in the Conversion of Amino Alcohols into Morpholines

Sven P. Fritz; Amara Mumtaz; Muhammad Yar; Eoghan M. McGarrigle; Varinder K. Aggarwal

doi:10.1002/ejoc.201100337

Sulfinamides as Highly Effective Amine Protecting Groups and Their Use in the Conversion of Amino Alcohols into Morpholines

Sven P. Fritz, Amara Mumtaz, Muhammad Yar, Eoghan M. McGarrigle, Varinder K. Aggarwal^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

41 Citations (Scopus)

Abstract

1,2-Amino alcohols have been converted into morpholines by using sulfinamides as temporary protecting/activating groups on the amine. We have developed a procedure for the selective synthesis of monoprotected N-sulfinyl amino alcohols through a double sulfinylation/hydrolysis strategy. Following the reaction of the sulfinamides with bromoethyl-diphenylsulfonium triflate, protected morpholines were obtained in high yields. Subsequent treatment with HCl liberated the morpholine hydrochloride salts. The usefulness of this high yielding and efficient methodology has been demonstrated in the formal synthesis of the antidepressant drug (S,S)-reboxetine.

Original language	English
Pages (from-to)	3156-3164
Number of pages	9
Journal	European Journal of Organic Chemistry
Issue number	17
DOIs	https://doi.org/10.1002/ejoc.201100337
Publication status	Published - Jun 2011

Keywords

Nitrogen heterocycles
Amino alcohols
Sulfinamides
Annulation
Protecting groups
VINYL SULFONIUM SALTS
ASYMMETRIC-SYNTHESIS
TERT-BUTANESULFINAMIDE
SULFURYL CHLORIDE
STEREOSELECTIVE-SYNTHESIS
TOLUENESULFINIC ESTERS
SULFINYL CHLORIDES
CONVENIENT METHOD
TANDEM REACTIONS
DERIVATIVES

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NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS
Aggarwal, V. K. (Principal Investigator)
1/10/05 → 1/10/10
Project: Research

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title = "Sulfinamides as Highly Effective Amine Protecting Groups and Their Use in the Conversion of Amino Alcohols into Morpholines",

abstract = "1,2-Amino alcohols have been converted into morpholines by using sulfinamides as temporary protecting/activating groups on the amine. We have developed a procedure for the selective synthesis of monoprotected N-sulfinyl amino alcohols through a double sulfinylation/hydrolysis strategy. Following the reaction of the sulfinamides with bromoethyl-diphenylsulfonium triflate, protected morpholines were obtained in high yields. Subsequent treatment with HCl liberated the morpholine hydrochloride salts. The usefulness of this high yielding and efficient methodology has been demonstrated in the formal synthesis of the antidepressant drug (S,S)-reboxetine.",

keywords = "Nitrogen heterocycles, Amino alcohols, Sulfinamides, Annulation, Protecting groups, VINYL SULFONIUM SALTS, ASYMMETRIC-SYNTHESIS, TERT-BUTANESULFINAMIDE, SULFURYL CHLORIDE, STEREOSELECTIVE-SYNTHESIS, TOLUENESULFINIC ESTERS, SULFINYL CHLORIDES, CONVENIENT METHOD, TANDEM REACTIONS, DERIVATIVES",

author = "Fritz, {Sven P.} and Amara Mumtaz and Muhammad Yar and McGarrigle, {Eoghan M.} and Aggarwal, {Varinder K.}",

year = "2011",

month = jun,

doi = "10.1002/ejoc.201100337",

language = "English",

pages = "3156--3164",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "17",

}

TY - JOUR

T1 - Sulfinamides as Highly Effective Amine Protecting Groups and Their Use in the Conversion of Amino Alcohols into Morpholines

AU - Fritz, Sven P.

AU - Mumtaz, Amara

AU - Yar, Muhammad

AU - McGarrigle, Eoghan M.

AU - Aggarwal, Varinder K.

PY - 2011/6

Y1 - 2011/6

N2 - 1,2-Amino alcohols have been converted into morpholines by using sulfinamides as temporary protecting/activating groups on the amine. We have developed a procedure for the selective synthesis of monoprotected N-sulfinyl amino alcohols through a double sulfinylation/hydrolysis strategy. Following the reaction of the sulfinamides with bromoethyl-diphenylsulfonium triflate, protected morpholines were obtained in high yields. Subsequent treatment with HCl liberated the morpholine hydrochloride salts. The usefulness of this high yielding and efficient methodology has been demonstrated in the formal synthesis of the antidepressant drug (S,S)-reboxetine.

AB - 1,2-Amino alcohols have been converted into morpholines by using sulfinamides as temporary protecting/activating groups on the amine. We have developed a procedure for the selective synthesis of monoprotected N-sulfinyl amino alcohols through a double sulfinylation/hydrolysis strategy. Following the reaction of the sulfinamides with bromoethyl-diphenylsulfonium triflate, protected morpholines were obtained in high yields. Subsequent treatment with HCl liberated the morpholine hydrochloride salts. The usefulness of this high yielding and efficient methodology has been demonstrated in the formal synthesis of the antidepressant drug (S,S)-reboxetine.

KW - Nitrogen heterocycles

KW - Amino alcohols

KW - Sulfinamides

KW - Annulation

KW - Protecting groups

KW - VINYL SULFONIUM SALTS

KW - ASYMMETRIC-SYNTHESIS

KW - TERT-BUTANESULFINAMIDE

KW - SULFURYL CHLORIDE

KW - STEREOSELECTIVE-SYNTHESIS

KW - TOLUENESULFINIC ESTERS

KW - SULFINYL CHLORIDES

KW - CONVENIENT METHOD

KW - TANDEM REACTIONS

KW - DERIVATIVES

U2 - 10.1002/ejoc.201100337

DO - 10.1002/ejoc.201100337

M3 - Article (Academic Journal)

SN - 1434-193X

SP - 3156

EP - 3164

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 17

ER -

Sulfinamides as Highly Effective Amine Protecting Groups and Their Use in the Conversion of Amino Alcohols into Morpholines

Abstract

Keywords

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NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS

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