(3aR,7aS)-7a-(2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole → [(3S,4R)-3-amino-3-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]12[CH2:17][O:16][CH2:15][CH2:14][C@H:13]1[CH2:12][O:11][NH:10]2>[Zn].C(O)(=O)C>[NH2:10][C@:9]1([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[C@H:13]([CH2:12][OH:11])[CH2:14][CH2:15][O:16][CH2:17]1Participants
Procedure
(3aR,7aS)-7a-(2,4-Difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole (C10) (1.06 g, 4.39 mmol) was mixed with acetic acid (10 mL); after addition of zinc powder (3.74 g, 57.2 mmol), the reaction mixture was stirred for 18 hours. Insoluble material was removed via filtration, and the filtrate was concentrated under reduced pressure. The resulting paste was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, washed with saturated aqueous sodium chloride solution, and dried over magnesium sulfate. Filtration and removal of solvent under reduced pressure provided the product. Yield: 900 mg, 3.70 mmol, 84%. 1H NMR (400 MHz, CD3OD) δ 1.71-1.78 (m, 1H), 2.00-2.12 (m, 1H), 2.40-2.48 (m, 1H), 3.37-3.40 (m, 2H), 3.50 (d, J=11.5 Hz, 1H), 3.62 (ddd, J=12.7, 11.5, 2.7 Hz, 1H), 4.01 (dd, J=11.3, 2.0 Hz, 1H), 4.09-4.15 (m, 1H), 6.96-7.05 (m, 2H), 7.64-7.71 (m, 1H).
Workup
- customInsoluble material was removed via filtration
- concentrationthe filtrate was concentrated under reduced pressure
- washwashed with saturated aqueous sodium bicarbonate solution
- washwashed with saturated aqueous sodium chloride solution
- dry with materialdried over magnesium sulfate
- filtrationFiltration and removal of solvent under reduced pressure
- customprovided the product
Sources & evidence
- ORD record
- ord-3caa89e57f35491d827a988cba85fece
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933221B2
Reaction notes
Loading…