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

HRID 1256221노트

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HRID 1256221 반응식
[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]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidine

생성물 1

HCID 866649281,1-Dimethylethyl (1-trifluoromethanesulphonylpiperidin-4-yl)carbamate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-55bd18416942432db94e68621e464505
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461175B2

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