Triethylamine → (3S)-3-[2-(tert-Butyldimethylsilyloxy)ethyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

HRID 1917301Notes

Reaction equation

HRID 1917301 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([C@@:15]1([CH2:29][CH2:30][OH:31])[CH2:19][C:18](=[O:20])[N:17]([C@@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])[CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].FC(F)(F)S(O[Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C>[C:8]([O:12][C:13]([C@@:15]1([CH2:29][CH2:30][O:31][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:19][C:18](=[O:20])[N:17]([C@@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])[CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 67491029HCID 67491029, compound

Product 1

HCID 67490763(3S)-3-[2-(tert-Butyldimethylsilyloxy)ethyl]-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl esterYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (3.0 mL, 21.8 mmol) was added to a solution of (3S)-3-(2-hydroxyethyl)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (2.42 g, 7.25 mmol) in dichloromethane (70 mL), and the mixture was cooled to 0° C. tert-Butyldimethylsilyl trifluoromethanesulfonate (2.50 mL, 10.9 mmol) was added dropwise, and the mixture was stirred at the same temperature for 1.5 hours. After addition of an ice piece and stirring, the reaction solution was poured into a mixture of ethyl acetate (50 mL) and saturated sodium bicarbonate (50 mL), followed by extraction with ethyl acetate (200 mL, 100 mL). The organic layers were combined and washed with brine (50 mL). After drying over anhydrous sodium sulfate and filtration, the solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1→2:1) to give 2.84 g (88%) of the title compound as a white solid.

Workup

  1. additionwas added dropwise
  2. stirringstirring
  3. extractionfollowed by extraction with ethyl acetate (200 mL, 100 mL)
  4. washwashed with brine (50 mL)
  5. dry with materialAfter drying over anhydrous sodium sulfate and filtration
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1→2:1)

Sources & evidence

ORD record
ord-af69ea3039714f8e9d8b70f371f870bb
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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