Methanesulfonyl chloride → tert-Butyl 4-(2-((methanesulfonyl)oxy)ethyl)piperidine-1-carboxylate

HRID 419625

반응식

HRID 419625 반응식
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:17][S:18]([O:1][CH2:2][CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1)(=[O:20])=[O:19]

참가 물질

4

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

생성물 1

HCID 15229596tert-Butyl 4-(2-((methanesulfonyl)oxy)ethyl)piperidine-1-carboxylate수율 121.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

The reaction was prepared in 2 batches, with both batches purified together. The amounts of reactants and product reflect the sum of both batches. To 1,1-dimethylethyl 4-(2-hydroxyethyl)-1-piperidinecarboxylate (172 g, 750 mmol) in DCM (4 L) was added TEA (304 g, 1.50 mol). The mixture was cooled 0° C. and methanesulfonyl chloride (190 g, 827 mmol) was added dropwise. The reaction mixture was stirred at rt for 2 h. The reaction was determined to be complete by TLC. The reaction was diluted with DCM and washed with saturated Na2CO3 and the aqueous layer was separated. The organic layer was dried (Na2SO4), and rotovapped down to provide the title compound of Step B (280 g, 911 mmol, 61%). 1H NMR (400 MHz, CDCl3) δ 0.95-1.15 (m, 2H), 1.38 (s, 9H), 1.47-1.68 (m, 5H), 2.53-2.70 (m, 2H), 2.94 (s, 3H), 3.95-4.10 (m, 2H), 4.21 (t, J=8.8 Hz, 2H).

후처리

  1. customThe reaction was prepared in 2 batches, with both batches
  2. custompurified together
  3. washwashed with saturated Na2CO3
  4. customthe aqueous layer was separated
  5. dry with materialThe organic layer was dried (Na2SO4)

출처 및 근거

ORD 기록
ord-691f670c6320449195fd7d685f71ea6f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

연결된 노트

불러오는 중…