Alpha-Aminoadipic Acid → 6-(Tert-butyl-dimethyl-silanyloxymethyl)-piperidin-2-one
Reaction equation
N1C=CN=[CH:2]1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])(C)C.OCC1N[C:20](=[O:22])[CH2:19]CC1.N[CH:24]([CH2:28]CCC(O)=O)[C:25](O)=O.[CH3:34][N:35]([CH:37]=[O:38])C>CCOC(C)=O.C1C=CC=CC=1>[C:9]([SiH2:6][O:22][C:20]([CH3:19])([CH3:2])[CH:34]1[NH:35][C:37](=[O:38])[CH2:28][CH2:24][CH2:25]1)([CH3:12])([CH3:11])[CH3:10]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
Imidazole (1.16 g, 17.0 mmol) and tert-butyldimethylsilyl chloride (1.18 g, 7.85 mmol) were added sequentially to a solution of 6-hydroxymethyl-piperidin-2-one (prepared from racemic α-aminoadipic acid according to Huang, et al., Synth. Commun. 1989, 19, Preparation of Optically Pure ω-Hydroxymethyl Lactams, 3485-3496, 921 mg, 7.14 mmol) in DMF (10 mL) at 0° C. The reaction mixture was allowed to warm to rt and was stirred at rt for 17 h. Benzene and EtOAc (3:7, 200 mL) was added and the solution was washed with brine (3×50 mL). The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2→3% MeOH/CH2Cl2, gradient) afforded 1.53 g (88%) of 6-(tert-butyl-dimethyl-silanyloxymethyl)-piperidin-2-one as a white solid.
Workup
- washthe solution was washed with brine (3×50 mL)
- dry with materialThe organic phase was dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurification of the residue by flash column chromatography on silica gel (CH2Cl2→3% MeOH/CH2Cl2, gradient)
Sources & evidence
- ORD record
- ord-2c477b6b8f8449209ce01f4bfb07b713
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06747037B1
Reaction notes
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