1-Boc-piperidine-3-carboxaldehyde → Tert-butyl 3-(2-methoxyethenyl)-1-piperidinecarboxylate
Reaction equation
[Cl-].[CH3:2][O:3][CH2:4][PH3+].CC(C)([O-])C.[K+].[CH:12]([CH:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1)=O>C1COCC1>[CH3:2][O:3][CH:4]=[CH:12][CH:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:15]1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of methoxymethylphosphonium chloride (5.14 g, 15 mmol) in THF (18 mL) was added potassium tert-butoxide (1.98 g, 15 mmol) at 0° C., and the mixture was stirred at 0° C. for 0.5 hr. A solution of tert-butyl 3-formyl-1-piperidinecarboxylate (2.13 g, 10 mmol) in THF (8 mL) was added dropwise at −20° C., and the resulting mixture was stirred at 0° C. to room temperature overnight. The mixture was partitioned between toluene and water. The separated organic phase was washed with brine, dried over Na2SO4, filtered, and evaporated. Purification by column chromatography on silica gel (hexane/ethyl acetate=5/1) gave tert-butyl 3-(2-methoxyethenyl)-1-piperidinecarboxylate as a colorless oil (1.16 g, yield; 48%).
Workup
- stirringthe resulting mixture was stirred at 0° C. to room temperature overnight
- customThe mixture was partitioned between toluene and water
- washThe separated organic phase was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated
- customPurification by column chromatography on silica gel (hexane/ethyl acetate=5/1)
Sources & evidence
- ORD record
- ord-b49816b2e4b046529a35db16bffba11d
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07435743B2
Reaction notes
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