Triethylamine → Benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate

HRID 43935

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C(N(CC)CC)C>>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 8471Triethylamine

HCID 10387Benzyl chloroformate

HCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 21981786Benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylateYield 81.1%

Procedure

The same operation as in Example (227a) was performed using 4-[(tert-butoxycarbonyl)amino]piperidine (2.00 g, 9.99 mmol), benzyl chloroformate (2.14 mL, 15.0 mmol) and triethylamine (3.48 mL, 25.0 mmol), to obtain 2.71 g of the title compound as a white solid (81%).

Sources & evidence

ORD record: ord-62ef6d9df10048689be273132c9cefaf
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Linked notes

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