Tetrabutylammonium Fluoride → HCID 59511369, compound

HRID 1038016Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:21][C:22]([C:24]1([C:37](C)(C)[O:38][SiH2]C(C)(C)C)[CH2:28][CH2:27][N:26]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1)=[O:23])[CH3:20]>>[CH2:19]([O:21][C:22]([C:24]1([CH2:37][OH:38])[CH2:28][CH2:27][N:26]([CH2:29][C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[CH2:25]1)=[O:23])[CH3:20]

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 131728356HCID 131728356, compound

Product 1

HCID 59511369HCID 59511369, compoundYield 68%

Procedure

Tetrabutylammonium fluoride (1.8 ml, 1M in THF) was added to 1-tert-butoxycarbonylmethyl-3-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-3-carboxylic acid ethyl ester (726 mg, 1.8 mmol). The reaction solution was stirred for half hour and purified by column chromatography using solution of ethyl acetate in hexanes (1:1), then ethyl acetate to provide the title product (350 mg, 68%).

Workup

custompurified by column chromatography

Sources & evidence

ORD record: ord-9986c409aa9a45469bd19240391b2c4c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546404B2

Reaction notes

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