Triethylamine → Perhydro-l-pyrrolizinyl methanesulfonate

HRID 51529ノート

反応式

HRID 51529 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

HCID 22736254Perhydro-l-pyrrolizinyl methanesulfonate収率 66.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3d9f1a17265e42898567545c2cce11d4
出典データセット
uspto-grants-2004_03
特許番号
US06713474B2

反応ノート

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