Sodium borohydride → (2R)-4-(5-Hydroxymethyl-3-trifluoromethyl-pyridin-2-yl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17]([CH:24]=[O:25])=[CH:16][N:15]=2)[CH2:10][C@H:9]1[CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]([F:23])([F:21])[F:22])=[CH:18][C:17]([CH2:24][OH:25])=[CH:16][N:15]=2)[CH2:10][C@H:9]1[CH3:26])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (2R)-4-(5-formyl-3-trifluoromethyl-pyridin-2-yl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester from step (e) above (4.48 g, 12 mmol) in methanol (30 mL) was added portionwise NaBH4 (542 mg, 14.4 mmol, Aldrich) with stirring at 0° C. The mixture was stirred at 0° C. for 30 min and the solvent was removed in vacuo. The residure was dissolved in EtOAc (60 mL) and washed with water (20 mL) and brine (20 mL), dried over Na2SO4, and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography, eluting with 50% EtOAc/hexane to give the title compound as a gum. MS (ESI, pos. ion) m/e: 376 (M+1).
Workup
- stirringThe mixture was stirred at 0° C. for 30 min
- customthe solvent was removed in vacuo
- dissolutionThe residure was dissolved in EtOAc (60 mL)
- washwashed with water (20 mL) and brine (20 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- customThe solvent was removed in vacuo
- customthe residue was purified by silica gel column chromatography
- washeluting with 50% EtOAc/hexane
Sources & evidence
- ORD record
- ord-cbb09f95e9a2406e985e085ef771bb55
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026241B2
Reaction notes
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