Benzyl chloroformate → 1-Boc-4-Cbz-amino-piperidine

HRID 1425286Notes

Reaction equation

[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[C:15](Cl)([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(OCC)(=O)C>[CH2:18]([O:17][C:15]([NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of tert-butyl 4-aminopiperidine-1-carboxylate (1.2 g, 6 mmol) in dichloromethane (20 mL) was cooled to 0° C. Carbobenzoxy chloride (1.03 mL, 7.2 mmol) and diisopropylethylamine (3.15 mL, 18 mmol) were added at the same temperature, and the solution was stirred at 0° C. for one hour. The reaction solution was neutralized with saturated aqueous potassium carbonate solution, diluted with ethyl acetate, washed with brine, and dried over magnesium sulfate. Thereafter, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/1) to obtain 1.5 g of the title compound as a yellow oily substance (75%).

Workup

washwashed with brine
dry with materialdried over magnesium sulfate
customThereafter, the solvent was evaporated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-f2e743f978004d61ac807f8f897f0d30
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927588B2

Reaction notes

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