Reaction equation
[C:1]([O:5][C:6](=[O:29])[C@H:7]([CH2:18][CH:19]([CH:27]=O)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH:8][C:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].[CH3:30][NH2:31].C1COCC1>ClCCl>[C:1]([O:5][C:6](=[O:29])[C@H:7]([CH2:18][CH:19]([CH2:27][NH:31][CH3:30])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH:8][C:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred solution of 40 (6.1 g, 14.9 mmol) in dichloromethane (50 mL) was treated with 2 N methylamine-THF solution (10 mL) at 0° C. overnight. After removal of solvents, the residual oil was dissolved in methanol (80 mL) and placed in an ice-bath. To the above solution was added sodium borohydride in small portions over 30 min. The reaction solution was kept at 0° C. for 1 hour, and solvent was then evaporated. The residue was worked up with brine and dichloromethane. After separation, the organic phase was dried over anhydrous MgSO4, rotary evaporated and dried in vacuum. The crude amine 41 (5.4 g, 78%) was obtained as a light yellow glassy solid.
Workup
- customAfter removal of solvents
- dissolutionthe residual oil was dissolved in methanol (80 mL)
- customplaced in an ice-bath
- additionTo the above solution was added sodium borohydride in small portions over 30 min
- customsolvent was then evaporated
- customAfter separation
- dry with materialthe organic phase was dried over anhydrous MgSO4
- customrotary evaporated
- customdried in vacuum
Sources & evidence
- ORD record
- ord-581076baa3bd49d7840e6c654d9bdd43
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06855695B2
Linked notes
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