Chloroiodomethane → Benzyl 2-azabicyclo[3.1.0]hexane-2-carboxylate

HRID 132821ノート

反応式

HRID 132821 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH:15]=[CH:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([Zn]CC)C.ClCI>C(OCC)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]2[CH:15]1[CH2:16]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 11644ChloroiodomethaneHCID 11074472Benzyl 2,3-dihydro-1H-pyrrole-1-carboxylateHCID 178418750HCID 178418750、化合物

生成物 1

HCID 22250560Benzyl 2-azabicyclo[3.1.0]hexane-2-carboxylate収率 50%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

To a cold (0° C.) solution of 2,3-dihydro-pyrrole-1-carboxylic acid benzyl ester (example 4, step 5, 300 mg, 1.0 eq.) in diethyl ether was slowly added a solution of diethylzinc in hexanes (1M, 7 mL, 4.75 eq.), followed by chloroiodomethane (1.1 mL, 10 eq.). The reaction mixture was stirred 3 h at 0° C., allowed to warm up to room temperature and stirred an additional 3 h. The reaction mixture was partitioned between an aqueous solution of ammonium chloride and diethyl ether. The aqueous layer was extracted with diethyl ether and the combined organic layers were washed with brine, dried over sodium sulphate and evaporated in vacuo and purified on silica, eluting with a 1:1 to 1:3 gradient of cyclohexane/dichloromethane, to yield 160 mg (50%) of the desired product as colourless oil. MS (m/e): 218.5 (MH+, 100%)

後処理

  1. temperatureto warm up to room temperature
  2. stirringstirred an additional 3 h
  3. customThe reaction mixture was partitioned between an aqueous solution of ammonium chloride and diethyl ether
  4. extractionThe aqueous layer was extracted with diethyl ether
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo
  8. custompurified on silica
  9. washeluting with a 1:1 to 1:3 gradient of cyclohexane/dichloromethane

出典と根拠

ORDレコード
ord-a004bb7478dd48abae7f4a4db1d44c25
出典データセット
uspto-grants-2008_06
特許番号
US07388095B2

反応ノート

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