Benzyl Alcohol → 4-Benzyl 1-tert-butyl piperidine-1,4-dicarboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:17](O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Procedure
To a solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (35.94 mmol; 8.24 g) in dichloromethane (100 mL) was added benzyl alcohol (55.79 mmol; 4.73 mL), dimethylaminopyridine (0.72 mmol; 0.08 g) and dicyclohexylcarbodiimide (43.13 mmol; 8.27 g) and the resulting mixture was stirred for 3 hours at room temperature. The resulting solution was evaporated and the residue was dissolved in ethyl acetate (300 mL). The resulting solution was washed with a 1N hydrochloric acid solution (2×50 mL) and brine (50 mL), and dried over magnesium sulfate. After filtration and evaporation, the residue was purified via flash column chromatography ((eluent gradient: 0 to 50% EtOAc in heptane) to yield piperidine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester after evaporation. MS (ESI) m/z 320.19 [M+H]+.
Workup
- customThe resulting solution was evaporated
- dissolutionthe residue was dissolved in ethyl acetate (300 mL)
- washThe resulting solution was washed with a 1N hydrochloric acid solution (2×50 mL) and brine (50 mL)
- dry with materialdried over magnesium sulfate
- filtrationAfter filtration and evaporation
- customthe residue was purified via flash column chromatography ((eluent gradient: 0 to 50% EtOAc in heptane)
Sources & evidence
- ORD record
- ord-822f9a4444dd4988a4a27687b5b6524b
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08686152B2
Reaction notes
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