HCID 86650261, compound → [(2R*,5R*)-5-(3-amino-phenyl)-2,5-dimethyl-2-trifluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester

HRID 2196257Notes

Reaction equation

HRID 2196257 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[C@:9]([CH3:28])([C:24]([F:27])([F:26])[F:25])[O:10][CH2:11][C@:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21]=[N+]=[N-])[CH:16]=2)([CH3:14])[N:13]=1)([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[C@:9]([CH3:28])([C:24]([F:27])([F:25])[F:26])[O:10][CH2:11][C@:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=2)([CH3:14])[N:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86650261HCID 86650261, compound

Product 1

HCID 67979198[(2R*,5R*)-5-(3-amino-phenyl)-2,5-dimethyl-2-trifluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of [(2R*,5R*)-5-(3-azido-phenyl)-2,5-dimethyl-2-trifluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (0.82 g, 1.92 mmol) in EtOH (10 ml) was stirred in the presence of 10% Pd—C (0.1 g) under an atmosphere of hydrogen at 25° C. for 1.5 h. The catalyst was filtered off over Celite, evaporated and the residual oil was purified by flash-chromatography on silica gel (hexane/EtOAc 10:1 to 1:2) to provide the title compound as a colorless foam: TLC (hexane/EtOAc 1:1): Rf=0.43; HPLC RtH5=1.082 min; 1H NMR (360 MHz, CDCl3): δ 10.94 (s, 1H), 7.21 (t, 1H), 6.74 (d, 1H), 6.67 (d, 1H), 6.66 (s, 1H), 4.01 (s, 2H), 3.78 (broad s, 2H), 1.68 (s, 3H), 1.65 (s, 3H), 1.57 (s, 9H); ESIMS: 386, 388 [(M+H)+].

Workup

  1. filtrationThe catalyst was filtered off over Celite
  2. customevaporated
  3. customthe residual oil was purified by flash-chromatography on silica gel (hexane/EtOAc 10:1 to 1:2)

Sources & evidence

ORD record
ord-6cc3209532b74be5a6fe2843bc9e4447
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

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