tert-Butyldimethylsilyl chloride → (2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

HRID 458334Notes

Reaction equation

HRID 458334 reaction equation
C1CCN2C(=NCCC2)CC1.[CH3:12][O:13][C:14]([C@@H:16]1[CH2:20][C@@H:19]([OH:21])[CH2:18][N:17]1[S:22]([C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1)(=[O:24])=[O:23])=[O:15].[CH3:35][C:36]([Si:39](Cl)([CH3:41])[CH3:40])([CH3:38])[CH3:37]>C(#N)C>[CH3:12][O:13][C:14]([C@@H:16]1[CH2:20][C@@H:19]([O:21][Si:39]([C:36]([CH3:38])([CH3:37])[CH3:35])([CH3:41])[CH3:40])[CH2:18][N:17]1[S:22]([C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1)(=[O:24])=[O:23])=[O:15]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 7987003(2S,4R)-4-Hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 69429818(2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

29 ml (194 mmol, 1.6 eq) DBU were added to a suspension of 41.4 g (121.4 mmol) (2S,4R)-4-Hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester in 150 ml acetonitrile at 0° C. To the resulting solution 29.25 g (194 mmol, 1.6 eq) TBDMSCl were added in portions and the reaction was stirred at RT overnight. After concentrating the crude oil was purified by column chromatography with EtOAc/hexane 1:2 on silica gel to give 49.2 g (90%) (2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester.

Workup

  1. concentrationAfter concentrating the crude oil
  2. customwas purified by column chromatography with EtOAc/hexane 1:2 on silica gel

Sources & evidence

ORD record
ord-fb9a74a448874d60bbf7387030caf409
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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