(R)-tert-butyl 3-(N-methoxy-N-methylcarbamoyl)piperidine-1-carboxylate → (3R)-1-(tert-butoxycarbonyl)-3-(2-phenoxybenzoyl)piperidine
Reaction equation
CON(C)[C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5].[O:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[Li])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[C:15]([O:14][C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4](=[O:5])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[O:20][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:7]1)=[O:13])([CH3:16])([CH3:17])[CH3:18]Participants
4
Procedure
To a solution of (R)-tert-butyl 3-(N-methoxy-N-methylcarbamoyl)piperidine-1-carboxylate (4.40 g, 16.2 mmol) in anhydrous THF (18 mL) at −10° C., was added dropwise the solution of 2-phenoxyphenyllithium prepared in Step 1 (80 mL, 32 mmol). The mixture was then warmed to rt, and stirred until no starting material remained (˜30 min). The reaction was quenched with 1 N HCl (˜30 mL) and extracted with Et2O (4×10 mL). The combined organic layers were washed with sat'd aq NaHCO3 and brine, and dried over Na2SO4. The solvent was removed to give (3R)-1-(tert-butoxycarbonyl)-3-(2-phenoxybenzoyl)piperidine (7.44 g, quantitative).
Workup
- custom(˜30 min)
- customThe reaction was quenched with 1 N HCl (˜30 mL)
- extractionextracted with Et2O (4×10 mL)
- washThe combined organic layers were washed with sat'd aq NaHCO3 and brine
- dry with materialdried over Na2SO4
- customThe solvent was removed
Sources & evidence
- ORD record
- ord-7b37a33a218b4b9fb80f8c9ffd54372a
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455521B2
Reaction notes
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