tert-Butanol → Benzyl 3-(tert-butoxycarbonylamino)piperidine-1-carboxylate
Reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13](C(O)=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:22]([CH2:25]C)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.[CH3:44][C:45]([OH:48])([CH3:47])[CH3:46]>>[C:45]([O:48][C:25]([NH:22][CH:13]1[CH2:14][CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:12]1)=[O:34])([CH3:47])([CH3:46])[CH3:44]Participants
Procedure
To a solution of 1-[(benzyloxy)carbonyl]-3-piperidinecarboxylic acid (3.00 g, 11.4 mmol) and Et3N (1.56 mL, 11.4 mmol) in t-BuOH (30 mL) was added diphenyl phosphoryl azide (DPPA) (2.46 mL, 11.4 mmol), and the mixture was refluxed for 21 hrs. After cooled to room temperature, the mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and a saturated aqueous NaHCO3 solution. The organic phase was washed with a saturated aqueous NaHCO3 solution and brine, dried over Na2SO4, and concentrated under reduced pressure. Purification by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 3/1) gave benzyl 3-[(tert-butoxycarbonyl)amino]-1-piperidinecarboxylate as a solid (2.22 g, yield; 58%).
Workup
- temperaturethe mixture was refluxed for 21 hrs
- concentrationthe mixture was concentrated under reduced pressure
- customthe residue was partitioned between ethyl acetate
- washThe organic phase was washed with a saturated aqueous NaHCO3 solution and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customPurification by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 3/1)
Sources & evidence
- ORD record
- ord-566b7f4796dc476a9d477e87d9f823c2
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07232909B2
Reaction notes
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