Triethylamine → Perhydro-l-pyrrolizinyl methanesulfonate

HRID 51529노트

반응식

HRID 51529 반응식
[CH:1]1([OH:9])[CH:8]2[N:4]([CH2:5][CH2:6][CH2:7]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19].[Cl-].[NH4+].[Na]>ClCCl>[CH3:17][S:18]([O:9][CH:1]1[CH:8]2[N:4]([CH2:5][CH2:6][CH2:7]2)[CH2:3][CH2:2]1)(=[O:20])=[O:19]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 499482hexahydro-1H-pyrrolizin-1-olHCID 5360545Sodium

생성물 1

HCID 22736254Perhydro-l-pyrrolizinyl methanesulfonate수율 66.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

A mixture of perhydro-1-pyrrolizinol (0.5 g, 3.94 mmol) and triethylamine (0.60 g, 5.91 mmol) in dichloromethane (10 ml) was stirred at 0° C. under an atmosphere of nitrogen. Methanesulfonyl chloride (0.68 g, 5.91 mmol) was added, then the mixture was allowed to warm to ambient temperature and stirred for 8 hours. Saturated aqueous ammonium chloride (10 ml), dichloromethane (25 ml) and saturated aqueous sodium bicarboante (10 ml) were added. The organic layer was dried over magnesium sulfate filtered and the filtrate evaporated under reduced pressure to give a residue. Purification of the material by flash chromatography on silica gel using heptane/ethyl acetate (1:3) as an eluent yielded perhydro-l-pyrrolizinyl methanesulfonate (0.54 g): 1H NMR (DMSO-d6, 400 MHz) δ 4.96 (m, 1H), 3.61 (m, 1H), 2.9-3.3 (m, 6H), 2.35 (m, 1H), 1.55-2.25 (m, 6H).

후처리

  1. temperatureto warm to ambient temperature
  2. stirringstirred for 8 hours
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated under reduced pressure
  6. customto give a residue
  7. customPurification of the material by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-3d9f1a17265e42898567545c2cce11d4
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713474B2

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