Carbon Dioxide → Tert-butyl 3-(hydroxymethyl)-3-methylpiperidine-1-carboxylate
Reaction equation
CC(C[AlH]CC(C)C)C.C(=O)=O.C([O:15][C:16]([C:18]1([CH3:31])[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]1)=O)C.OS([O-])(=O)=O.[K+]>C1COCC1>[C:27]([O:26][C:24]([N:20]1[CH2:21][CH2:22][CH2:23][C:18]([CH2:16][OH:15])([CH3:31])[CH2:19]1)=[O:25])([CH3:30])([CH3:29])[CH3:28]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
6.14 ml (1.2 M in toluene, 7.37 mmol) of DIBALH was dropped to a dry ice cooled (−30° C.) solution of 1.00 g (3.69 mmol) crude 3-methyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester in 2 ml of THF. The reaction was warmed up (0° C. for 1 h), continued for 3 h, cooled (−15° C.) and treated again with 0.61 ml (1.2 M in toluene, 0.74 mmol) of DIBALH. After 1 h the reaction was warmed up to 0° C. and neutralized with aqueous 10% KHSO4 solution. The mixture was extracted with ether (3×), the organic phases were washed with a aqueous 10% NaCl solution, dried (Na2SO4) and evaporated to give after flash silica gel column (n-heptane/EtOAc 9:1) 0.61 g (73%) of the title compound as yellow oil. MS: 230.0 (MH+).
Workup
- temperaturecooled (−15° C.)
- extractionThe mixture was extracted with ether (3×)
- washthe organic phases were washed with a aqueous 10% NaCl solution
- dry with materialdried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-97245c07b29246aea16f31afc06ea9de
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07632829B2
Reaction notes
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