Telescoped approach to aryl hydroxymethylation in the synthesis of a key pharmaceutical intermediate

Catherine N. Slattery; Rebecca E. Deasy; Anita R. Maguire; Michael E. Kopach; Utpal K. Singh; Mark D. Argentine; William G. Trankle; Roger Brian Scherer; Humphrey Moynihan

doi:10.1021/jo400647t

Telescoped approach to aryl hydroxymethylation in the synthesis of a key pharmaceutical intermediate

Catherine N. Slattery
, Rebecca E. Deasy
, Anita R. Maguire
, Michael E. Kopach
, Utpal K. Singh
, Mark D. Argentine
, William G. Trankle
, Roger Brian Scherer
, Humphrey Moynihan

Eli Lilly
Eli Lilly SA

Research output: Contribution to journal › Article › peer-review

Abstract

An efficient synthetic approach leading to introduction of the hydroxymethyl group to an aryl moiety via combination of the Bouveault formylation and hydride reduction has been optimized using a rational, mechanistic-based approach. This approach enabled telescoping of the two steps into a single efficient process, readily amenable to scaleup.

Original language	English
Pages (from-to)	5955-5963
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	78
Issue number	12
DOIs	https://doi.org/10.1021/jo400647t
Publication status	Published - 21 Jun 2013

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https://hdl.handle.net/10468/2998Licence: CC BY-NC-ND

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title = "Telescoped approach to aryl hydroxymethylation in the synthesis of a key pharmaceutical intermediate",

abstract = "An efficient synthetic approach leading to introduction of the hydroxymethyl group to an aryl moiety via combination of the Bouveault formylation and hydride reduction has been optimized using a rational, mechanistic-based approach. This approach enabled telescoping of the two steps into a single efficient process, readily amenable to scaleup.",

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AU - Slattery, Catherine N.

AU - Deasy, Rebecca E.

AU - Maguire, Anita R.

AU - Kopach, Michael E.

AU - Singh, Utpal K.

AU - Argentine, Mark D.

AU - Trankle, William G.

AU - Scherer, Roger Brian

AU - Moynihan, Humphrey

PY - 2013/6/21

Y1 - 2013/6/21

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AB - An efficient synthetic approach leading to introduction of the hydroxymethyl group to an aryl moiety via combination of the Bouveault formylation and hydride reduction has been optimized using a rational, mechanistic-based approach. This approach enabled telescoping of the two steps into a single efficient process, readily amenable to scaleup.

UR - https://www.scopus.com/pages/publications/84879348422

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SP - 5955

EP - 5963

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 12

ER -

Telescoped approach to aryl hydroxymethylation in the synthesis of a key pharmaceutical intermediate

Abstract

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