Trifluoroacetic acid → (2S)-2-(4,4,5,5,5-pentafluoropentylthiomethyl)-pyrrolidine

HRID 361690Notes

Reaction equation

HRID 361690 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][S:14][CH2:15][CH2:16][CH2:17][C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>>[F:24][C:18]([F:23])([C:19]([F:20])([F:21])[F:22])[CH2:17][CH2:16][CH2:15][S:14][CH2:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57019942N-tert-butyloxycarbonyl-(2S)-2-(4,4,5,5,5-pentafluoropentylthiomethyl)-pyrrolidine

Product 1

HCID 57069197(2S)-2-(4,4,5,5,5-pentafluoropentylthiomethyl)-pyrrolidineYield 96.1%

Conditions

Temperature
0 °C

Procedure

2.55 g of N-tert-butyloxycarbonyl-(2S)-2-(4,4,5,5,5-pentafluoropentylthiomethyl)-pyrrolidine is added to 5.4 ml of trifluoroacetic acid, cooled to 0° C., and the mixture is stirred for 1.5 hours at 0° C. and for 16 hours at room temperature. The reaction mixture is poured onto 10% sodium bicarbonate solution, extracted with ethyl acetate, washed with saturated common salt solution, dried on sodium sulfate and concentrated by evaporation. 1.8 g of the title compound is obtained as oily crude product.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated common salt solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-bae9160acd8545f2a18d0d41a3ee7a8c
Source dataset
uspto-grants-1999_02
Patent number
US05866560

Reaction notes

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