Acetic Acid → Methyl (3S,4R)-4-(2,4-difluorophenyl)-1-isopropylpyrrolidine-3-carboxylate
Reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[CH3:19][C:20]([CH3:22])=O.[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[C@@H:31]1[CH2:35][NH:34][CH2:33][C@H:32]1[C:36]([O:38][CH3:39])=[O:37].C(=O)([O-])O.[Na+]>ClCCl.[Cl-].[Na+].O>[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[C@@H:31]1[CH2:35][N:34]([CH:20]([CH3:22])[CH3:19])[CH2:33][C@H:32]1[C:36]([O:38][CH3:39])=[O:37]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
Sodium triacetoxyborohydride (1.32 g, 6.22 mmol) and acetic acid (235 μL, 4.14 mmol) were added to a solution of acetone (304 μL, 4.14 mmol) and methyl (3S,4R)-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate, from preparation 31 (1 g, 4.14 mmol) in dichloromethane (20 mL) at room temperature. The resulting mixture was stirred for 2 hours and diluted with dichloromethane (10 mL). Aqueous sodium hydrogen carbonate solution was added (2×20 mL) followed by brine (20 mL). The phases were separated, the organic phase was dried over magnesium sulfate, filtered and the solvent was removed in vacuo to give the crude residue. Purification of the residue by column chromatography using dichloromethane:methanol (99:1-98:2) as eluent afforded the desired product, 1.01 g (86%).
Workup
- customThe phases were separated
- dry with materialthe organic phase was dried over magnesium sulfate
- filtrationfiltered
- customthe solvent was removed in vacuo
- customto give the crude residue
- customPurification of the residue by column chromatography
Sources & evidence
- ORD record
- ord-2e16f5cf4a8a4818b8784bfc91aa6392
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07649002B2
Reaction notes
Loading…