Methane → (S)-3-[(S)-2-Amino-1-(4-trifluoromethylphenoxy)ethyl]pyrrolidine-1-carboxylic Acid t-Butyl Ester

HRID 1889141Notes

Reaction equation

HRID 1889141 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([C@H:13]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[CH2:14][N:15]=[N+]=[N-])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C.O>[Pd].CCO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([C@H:13]([O:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:23][CH:24]=2)[CH2:14][NH2:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 297MethaneHCID 962WaterHCID 86666089(S)-3-[(S)-2-Azido-1-(4-trifluoromethylphenoxy)ethyl]pyrrolidine-1-carboxylic acid t-butyl ester

Product 1

HCID 67776985(S)-3-[(S)-2-Amino-1-(4-trifluoromethylphenoxy)ethyl]pyrrolidine-1-carboxylic Acid t-Butyl EsterYield 91.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

(S)-3-[(S)-2-Azido-1-(4-trifluoromethylphenoxy)ethyl]pyrrolidine-1-carboxylic acid t-butyl ester (2.10 g, 5.24 mmol) was combined with 10% Pd/C, Degussa type, wet 50% (0.05:0.45:0.5, Palladium:carbon black:H2O, 1.1 g, 520 μmol) and EtOH (240 mL). The mixture was stirred under an atmosphere of hydrogen (1 atm) at room temperature for 1 hour. The catalyst was then removed by filtration through Celite (MeOH wash) and the filtrate was concentrated to yield the title compound (1.8 g).

Workup

  1. customThe catalyst was then removed by filtration through Celite (MeOH wash)
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6e86b91352d34e0b910ca1778963f628
Source dataset
uspto-grants-2013_08
Patent number
US08501964B2

Reaction notes

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