Acetic Acid → [1-Cyclopropylmethyl-4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester
Reaction equation
[CH2:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][C:9]1([C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=2)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[CH:2]([CH3:4])[CH3:3].[CH:23]1([CH:26]=O)[CH2:25][CH2:24]1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)CCl.CCOC(C)=O>[CH2:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][C:9]1([C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=2)[CH2:10][CH2:11][N:12]([CH2:26][CH:23]2[CH2:25][CH2:24]2)[CH2:13][CH2:14]1)[CH:2]([CH3:4])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of [4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester (0.058 g, 0.14 mmol) in ClCH2CH2Cl (0.75 mL) at room temperature under Ar was added cyclopropanecarboxaldehyde (0.012 mL, 0.156 mmol, 1.2 eq.) and HOAc (0.075 mL, 1% v/v). The mixture was stirred for 0.5 h then Na(OAc)3BH (0.041 g, 0.2 mmol, 1.5 eq.) was added. The mixture was stirred for 16 h, diluted with EtOAc (10 mL) and washed with saturated aqueous NaHCO3 solution (10 mL) and saturated brine (10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated by rotary evaporation to give [1-cyclopropylmethyl-4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-carbamic acid isobutyl ester (0.061 g, 95%). MS (ESI): 471.2/472.2 (M+1).
Workup
- stirringThe mixture was stirred for 16 h
- washwashed with saturated aqueous NaHCO3 solution (10 mL) and saturated brine (10 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated by rotary evaporation
Sources & evidence
- ORD record
- ord-80f1b748a94744599a9a9407eacaa0f0
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06887889B2
Reaction notes
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