Triethylamine → 1,1-Dimethylethyl (1-trifluoromethanesulphonylpiperidin-4-yl)carbamate

HRID 1256221Notes

Reaction equation

[CH3:1][C:2]([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].C(N(CC)CC)C.[F:22][C:23]([F:29])([F:28])[S:24](Cl)(=[O:26])=[O:25].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:22][C:23]([F:29])([F:28])[S:24]([N:12]1[CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:14][CH2:13]1)(=[O:26])=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

A 150 ml round-bottomed flask equipped with a magnetic stirrer is charged under argon with 2 g of 4-N-boc-aminopiperidine in 35 ml of DCM, 82 mg of 4-dimethylaminopyridine (DMAP) and 1.86 ml of triethylamine. After cooling to 0° C. using an ice bath, 1.6 ml of trifluoromethanesulphonyl chloride are added dropwise. The mixture is stirred at 0° C. for 30 min and then at RT for 1 h. It is poured into 100 ml of saturated aqueous sodium bicarbonate solution. It is extracted with AcOEt, washed with saturated aqueous NaCl solution, dried over MgSO4, filtered and concentrated to dryness under RP. Chromatography on silica gel (15-40 μm), eluting with a mixture of DCM and methanol (98/02 by vol.), gives 1.5 g of 1,1-dimethylethyl (1-trifluoromethanesulphonylpiperidin-4-yl)carbamate (cream solid). MS (E/I): m/z=232 (M+).

Workup

customA 150 ml round-bottomed flask equipped with a magnetic stirrer
waitat RT for 1 h
extractionIt is extracted with AcOEt
washwashed with saturated aqueous NaCl solution
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to dryness under RP
washChromatography on silica gel (15-40 μm), eluting with a mixture of DCM and methanol (98/02 by vol.)

Sources & evidence

ORD record: ord-55bd18416942432db94e68621e464505
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461175B2

Reaction notes

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