Trifluoroacetic acid → (1S,2S)-1-(3,5-Bis-trifluoromethyl-benzyloxymethyl)-2-phenyl-3-aza-bicyclo[3.1.0]hexane

HRID 1295361Notes

Reaction equation

HRID 1295361 reaction equation
C(OC([N:8]1[CH2:13][CH:12]2[C@@:10]([CH2:14][O:15][CH2:16][C:17]3[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=3)([CH2:11]2)[C@@H:9]1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:29][C:27]([F:28])([F:30])[C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=1)[CH2:16][O:15][CH2:14][C@@:10]12[CH2:11][CH:12]1[CH2:13][NH:8][C@H:9]2[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 86602047(1S,2S)-1-(3,5-bis-trifluoromethyl-benzyloxymethyl)-2-phenyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

Product 1

HCID 86602046(1S,2S)-1-(3,5-Bis-trifluoromethyl-benzyloxymethyl)-2-phenyl-3-aza-bicyclo[3.1.0]hexaneYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask containing racemic Intermediate 24, one enantiomer being (1S,2S)-1-(3,5-bis-trifluoromethyl-benzyloxymethyl)-2-phenyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (0.25 g, 0.49 mmol) and methylene chloride (10 mL) was immersed in a 0° C. bath. Trifluoroacetic acid (0.75 mL, 9.7 mmol) was added, and the reaction was stirred for 3 hours at room temperature. 20% NaOH solution was added cautiously and then saturated sodium bicarbonate solution was added until the pH=8. The phases were separated; the organics were washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound (0.20 g, quantitative yield).

Workup

  1. customwas immersed in a 0° C.
  2. customThe phases were separated
  3. washthe organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-20190669f10d46379557a51f007dd01e
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

Loading…