Triethylamine → Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

HRID 15519

반응식

HRID 15519 반응식
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.CCN(CC)CC.[CH3:23][S:24](Cl)(=[O:26])=[O:25].CCOC(C)=O>C1COCC1.O>[CH3:23][S:24]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)(=[O:26])=[O:25]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

생성물 1

HCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate수율 98.9%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (Aldrich) (4.30 g, 20 mmol) and Et3N (5 mL) in THF (60 mL) at 0° C. was added MeSO2Cl (1.6 mL) dropwise with stirring. After 2.5 h EtOAc (160 mL) and water (50 mL) were added to the reaction mixture, the EtOAc layer was separated, washed with 1N HCl (30 mL), dried over MgSO4, concentrated in vacuo to obtain the product (5.8 g, 98.9%) as a low melting white solid. This material was used directly for the next step without any further purification. 1H NMR (CDCl3) δ 4.20 (m, 2H), 4.04 (d, 2H, J=6.1 Hz), 2.99 (s, 3H), 2.68 (m, 2H), 2.01-1.70 (m, 3H), 1.43 (s, 9H), 1.20 (m, 2H).

후처리

  1. customthe EtOAc layer was separated
  2. washwashed with 1N HCl (30 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6a1b5ad903a543eab3bf4a269d1eb3a3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732613B2

연결된 노트

불러오는 중…