Water → 3-Carbamoyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 659609Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)OCC(C)C.[NH3:25].O.O>C1COCC1>[C:14]([CH:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)(=[O:16])[NH2:25]

Participants

Conditions

Temperature: 10 °C

Procedure

A 1-L 3-necked round-bottomed flask was charged with a solution of 1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (10 g, 42.79 mmol, 1.00 equiv, 98%), TEA (5.2 g, 50.46 mmol, 1.18 equiv, 98%) in THF (100 mL). To this mixture was added isobutyl carbonochloridate (6.8 g, 49.00 mmol, 1.15 equiv, 98%) drop wise at 10° C. The resulting solution was stirred for 15 minutes at 10° C. in a water/ice bath. Then, to the mixture was added NH3.H2O (25%, 60 mL) and allowed to stir for 10 minutes at 10° C. Then, it was treated with water (40 mL) to afford off-white solids after filtration. The solid was dried in an oven under reduced pressure affording tert-butyl 3-carbamoylpiperidine-1-carboxylate as white solid (7 g, 72%).

Workup

stirringto stir for 10 minutes at 10° C
customto afford off-white solids
filtrationafter filtration
customThe solid was dried in an oven under reduced pressure

Sources & evidence

ORD record: ord-d93a86697c56440da9d3e2a908379a45
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080566B1

Reaction notes

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