Trifluoroacetic acid → HCID 67439028, compound

HRID 1874622Notes

Reaction equation

HRID 1874622 reaction equation
[OH:1][C:2]([CH3:26])([CH3:25])[C@H:3]([NH:17]C(=O)OC(C)(C)C)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]([CH3:16])[CH2:13][CH2:14][CH3:15])=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O>ClCCl>[NH2:17][C@H:3]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][CH:12]([CH3:16])[CH2:13][CH2:14][CH3:15])=[CH:8][CH:9]=1)[C:2]([CH3:26])([OH:1])[CH3:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86658395HCID 86658395, compound

Product 1

HCID 67439028HCID 67439028, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl (1R)-2-hydroxy-2-methyl-1-(4-(2-methylpentyloxy)phenyl)-propylcarbamate (340 mg, 0.930 mmol) in dichloromethane (1 mL) was added TFA (2 mL, 26.0 mmol). The reaction mixture was stirred at room temperature for 1 h. The solvent was evaporated and the residue was transferred to a separatory funnel containing saturated aqueous K2CO3 solution. The aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were concentrated to afford (1R)-1-amino-2-methyl-1-(4-(2-methylpentyloxy)phenyl)propan-2-ol.TFA (350 mg, 99% yield) as a colorless oil which was used directly in the next step: 1H NMR (400 MHz, CDCl3) δ 7.20 (d, J=8.6 Hz, 2H), 6.82 (d, J=8.8 Hz, 2H), 3.78 (dd, J=9.1, 5.8 Hz, 1H), 3.73 (s, 1H), 3.68 (dd, J=8.9, 6.7 Hz, 1H), 1.86-1.97 (m, 1H), 1.27-1.51 (m, 4H), 1.17 (s, 3H), 1.01 (s, 3H), 0.99 (d, J=6.8 Hz, 3H), 0.90 (t, J=7.3 Hz, 3H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was transferred to a separatory funnel
  3. additioncontaining saturated aqueous K2CO3 solution
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  5. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-9f02385a4f954aadbbbcc6a011a73802
Source dataset
uspto-grants-2012_11
Patent number
US08304577B2

Reaction notes

Loading…