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

HRID 650383Notes

Reaction equation

HRID 650383 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-6fa4c0dc515d4ef0ae05e79645376515
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

Loading…