Triethylamine → Benzyl 3-(3-hydroxypropyl)piperidine-1-carboxylate
Reaction equation
[C:1]1([CH2:7][O:8][C:9]([O:11]N2C(=O)CCC2=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH:21]([CH2:25][CH2:26][CH2:27][OH:28])[CH2:20]1.C(N(CC)CC)C>ClCCl>[OH:28][CH2:27][CH2:26][CH2:25][CH:21]1[CH2:22][CH2:23][CH2:24][N:19]([C:9]([O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:11])[CH2:20]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1-({[(Phenylmethyl)oxy]carbonyl}oxy)-2,5-pyrrolidinedione (8.70 g), 34.9 mmol) was added portionwise to a stirred mixture of 3-(3-piperidinyl)-1-propanol (5.02 g, 35 mmol) and triethylamine (5 ml, 3.63 g, 35.9 mmol) in dichloromethane (100 ml) at room temperature. The resultant mixture was allowed to stand at room temperature for 18 hours. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate (100 ml). The organic phase was dried (MgSO4), filtered and evaporated. The sample was purified by chromatography on silica (100 g cartridge loaded in dichloromethane) using a gradient of 0-100% ethyl acetate-cyclohexane over 40 mins. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a colourless liquid (8.45 g).
Workup
- washThe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate (100 ml)
- dry with materialThe organic phase was dried (MgSO4)
- filtrationfiltered
- customevaporated
- customThe sample was purified by chromatography on silica (100 g cartridge loaded in dichloromethane)
- customover 40 mins
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-3965ac8aeb924d249e92de8f6893a57e
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802684B2
Reaction notes
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