Enantioenriched synthesis of Escitalopram using lithiation-borylation methodology

Benjamin M. Partridge; Stephen P. Thomas; Varinder K. Aggarwal

doi:10.1016/j.tet.2011.09.142

Enantioenriched synthesis of Escitalopram using lithiation-borylation methodology

Benjamin M. Partridge, Stephen P. Thomas, Varinder K. Aggarwal^*

^*Corresponding author for this work

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

13 Citations (Scopus)

Abstract

The asymmetric synthesis of Escitalopram has been completed using a lithiation-borylation reaction as the key step. Suitably functionalized enantioenriched carbamate (er 98:2) and boronic ester coupling partners were prepared and following deprotonation with s-BuLi and borylation, the tertiary alcohol was obtained in 42% yield and 93:7 er. The lithiation-borylation reaction was found to tolerate nitrile, benzylic alcohol and N-Boc functionalities. The tertiary alcohol was converted to Escitalopram in three further steps. (C) 2011 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	10082-10088
Number of pages	7
Journal	Tetrahedron
Volume	67
Issue number	52
DOIs	https://doi.org/10.1016/j.tet.2011.09.142
Publication status	Published - 30 Dec 2011

Keywords

Lithiation-borylation
Escitalopram
Total synthesis
Carbamate
Boronic ester
ENANTIOSELECTIVE ADDITION
SECONDARY ALCOHOLS
BORONIC ESTERS
CONVERSION
ALDEHYDES
RESOLUTION

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10.1016/j.tet.2011.09.142

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

Cite this

@article{d275f01dc58e4382a5aabab3d9c6d676,

title = "Enantioenriched synthesis of Escitalopram using lithiation-borylation methodology",

abstract = "The asymmetric synthesis of Escitalopram has been completed using a lithiation-borylation reaction as the key step. Suitably functionalized enantioenriched carbamate (er 98:2) and boronic ester coupling partners were prepared and following deprotonation with s-BuLi and borylation, the tertiary alcohol was obtained in 42% yield and 93:7 er. The lithiation-borylation reaction was found to tolerate nitrile, benzylic alcohol and N-Boc functionalities. The tertiary alcohol was converted to Escitalopram in three further steps. (C) 2011 Elsevier Ltd. All rights reserved.",

keywords = "Lithiation-borylation, Escitalopram, Total synthesis, Carbamate, Boronic ester, ENANTIOSELECTIVE ADDITION, SECONDARY ALCOHOLS, BORONIC ESTERS, CONVERSION, ALDEHYDES, RESOLUTION",

author = "Partridge, {Benjamin M.} and Thomas, {Stephen P.} and Aggarwal, {Varinder K.}",

year = "2011",

month = dec,

day = "30",

doi = "10.1016/j.tet.2011.09.142",

language = "English",

volume = "67",

pages = "10082--10088",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "52",

}

TY - JOUR

T1 - Enantioenriched synthesis of Escitalopram using lithiation-borylation methodology

AU - Partridge, Benjamin M.

AU - Thomas, Stephen P.

AU - Aggarwal, Varinder K.

PY - 2011/12/30

Y1 - 2011/12/30

N2 - The asymmetric synthesis of Escitalopram has been completed using a lithiation-borylation reaction as the key step. Suitably functionalized enantioenriched carbamate (er 98:2) and boronic ester coupling partners were prepared and following deprotonation with s-BuLi and borylation, the tertiary alcohol was obtained in 42% yield and 93:7 er. The lithiation-borylation reaction was found to tolerate nitrile, benzylic alcohol and N-Boc functionalities. The tertiary alcohol was converted to Escitalopram in three further steps. (C) 2011 Elsevier Ltd. All rights reserved.

AB - The asymmetric synthesis of Escitalopram has been completed using a lithiation-borylation reaction as the key step. Suitably functionalized enantioenriched carbamate (er 98:2) and boronic ester coupling partners were prepared and following deprotonation with s-BuLi and borylation, the tertiary alcohol was obtained in 42% yield and 93:7 er. The lithiation-borylation reaction was found to tolerate nitrile, benzylic alcohol and N-Boc functionalities. The tertiary alcohol was converted to Escitalopram in three further steps. (C) 2011 Elsevier Ltd. All rights reserved.

KW - Lithiation-borylation

KW - Escitalopram

KW - Total synthesis

KW - Carbamate

KW - Boronic ester

KW - ENANTIOSELECTIVE ADDITION

KW - SECONDARY ALCOHOLS

KW - BORONIC ESTERS

KW - CONVERSION

KW - ALDEHYDES

KW - RESOLUTION

U2 - 10.1016/j.tet.2011.09.142

DO - 10.1016/j.tet.2011.09.142

M3 - Article (Academic Journal)

VL - 67

SP - 10082

EP - 10088

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 52

ER -

Enantioenriched synthesis of Escitalopram using lithiation-borylation methodology

Abstract

Keywords

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NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS

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