Sodium Bicarbonate → (2S)-2-(4-trifluoromethylphenylthiomethyl)-pyrrolidine

HRID 650387Notes

Reaction equation

HRID 650387 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][S:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)=O)(C)(C)C.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[F:24][C:21]([F:22])([F:23])[C:18]1[CH:17]=[CH:16][C:15]([S:14][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 69338860N-tert-butyloxycarbonyl-(2S)-2-(4-trifluoromethylphenylthiomethyl)-pyrrolidine

Product 1

HCID 57133071(2S)-2-(4-trifluoromethylphenylthiomethyl)-pyrrolidineYield 30.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2.55 g of N-tert-butyloxycarbonyl-(2S)-2-(4-trifluoromethylphenylthiomethyl)-pyrrolidine in 5.64 ml of trifluoroacetic acid is stirred for 1 hour at 0° C. and then for 3.5 hours at room temperature. The reaction mixture is poured onto 10% sodium bicarbonate solution, extracted with ethyl acetate, washed twice with 2 M hydrochloric acid, the water phase is extracted with ether, made basic with sodium bicarbonate, extracted three times with ethyl acetate, washed with common salt solution, dried on sodium sulfate and concentrated by evaporation. 557 mg of (2S)-2-(4-trifluoromethylphenylthio-methyl)-pyrrolidine is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed twice with 2 M hydrochloric acid
  3. extractionthe water phase is extracted with ether
  4. extractionextracted three times with ethyl acetate
  5. washwashed with common salt solution
  6. customdried on sodium sulfate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-fec040b384d24d21b03cf1e807ccb037
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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