HCID 59458516, compound → (S)-2-amino-1-phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)ethanol

HRID 1874244Notes

Reaction equation

HRID 1874244 reaction equation
[N:1]([C:4]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:34])([F:33])[F:32])[CH:25]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:23])([F:22])[F:21])[CH:14]=1)[C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:6])=[N+]=[N-]>CO.[Pd]>[NH2:1][C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:21])([F:22])[F:23])[CH:14]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:33])([F:34])[F:32])[CH:25]=1)[C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:6]

Participants

4

Reactant 1

HCID 59458516HCID 59458516, compound

Product 1

HCID 59459057(S)-2-amino-1-phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)ethanolYield 87.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A slurry of (S)-2-azido-1-phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)ethanol (64 mg, 0.132 mmol) and 10% Pd on C (40 mg) in methanol (2 mL) was subjected to balloon hydrogenation overnight at rt. The reaction mixture was filtered through celite and the filtrate was concentrated to give (S)-2-amino-1-phenyl-2,2-bis(3-(trifluoromethoxy)phenyl)ethanol as a light yellow oil (53 mg, 87% yield). HPLC: RT=3.40 min (Phenomenex Luna C18 5 u column, eluting with 10-90% MeOH/H2O containing 0.1% phosphoric acid over a 4 minute gradient, monitoring at 220 nm). LCMS: [M+H] 458.1 (Phenomenex Luna C18 column, 4.6×30 mm eluting with 10-90% MeOH/H2O over 2 minutes containing 0.1% TFA; 5 mL/min, monitoring at 220 nm).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6d1e7629bc0b42049d5040f7705844d1
Source dataset
uspto-grants-2012_11
Patent number
US08304403B2

Reaction notes

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