HCID 59485770, compound → HCID 59486034, compound

HRID 1972231Notes

Reaction equation

HRID 1972231 reaction equation
[OH:1][CH2:2][C@H:3]([NH:14]C(=O)OCC1C=CC=CC=1)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1>CO.[Pd]>[NH2:14][C@H:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:5]=1)[CH2:2][OH:1]

Participants

4

Reactant 1

HCID 59485770HCID 59485770, compound

Product 1

HCID 59486034HCID 59486034, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (R)-Benzyl 2-hydroxy-1-(3-(trifluoromethyl)phenyl)ethylcarbamate (4.54 g, 13.4 mmol) in MeOH (100 mL) is slowly added 10 wt % Pd/C (454 mg). The reaction mixture is stirred at room temperature under hydrogen (balloon) for 1.5 h, filtered through celite, and evaporated in vacuo to provide crude (R)-2-amino-2-(3-(trifluoromethyl)phenyl)ethanol (2.70 g, 98% yield) as a white solid product; 1H NMR (CDCl3, 400 MHz) δ 7.62 (s, 1H), 7.55 (m, 2H), 7.47 (t, 1H), 4.15 (dd, 1H), 3.77 (dd, 1H), 3.57 (dd, 1H); HPLC-MS calculated for C9H10F3NO (M+H+) 206.1, found 206.1.

Workup

  1. filtrationfiltered through celite
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-f34746e359b949bfa5deaf478fdb8bd9
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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