1,4-Dibromobutane → cis-(2-Pyrrolidin-1-yl-cyclohexyl)-carbamic acid tert-butyl ester

HRID 659182

反応式

HRID 659182 の反応式
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]1[C@H:14]([NH2:15])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26]Br>C(#N)C>[C:2]([O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@@H:14]1[N:15]1[CH2:26][CH2:25][CH2:24][CH2:23]1)([CH3:1])([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protected

生成物 1

HCID 66680888cis-(2-Pyrrolidin-1-yl-cyclohexyl)-carbamic acid tert-butyl ester収率 88.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

1-N-Boc-1,2-cis-cyclohexyldiamine 5 (CAS 184954-75-4) (1.65 g, 7.7 mmol) was dissolved in 100 mL acetonitrile. Potassium carbonate (5.3 g, 39 mmol) and 1,4-dibromobutane (2.8 g, 13 mmol) were added and the reaction mixture was refluxed overnight. The solvent was evaporated off. The residue was taken up in water and ethyl acetate and was extracted three times with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0→140:10:1) yielded cis-(2-pyrrolidin-1-yl-cyclohexyl)-carbamic acid tert-butyl ester as a yellow liquid (1.82 g, 88%), MS: m/e=269.4 [(M+H)+].

後処理

  1. temperaturethe reaction mixture was refluxed overnight
  2. customThe solvent was evaporated off
  3. extractionethyl acetate and was extracted three times with ethyl acetate
  4. customThe combined organic phases were dried on sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0→140:10:1)

出典と根拠

ORDレコード
ord-9cf38beef3ff40eebc6de1ccba63f616
出典データセット
uspto-grants-2011_12
特許番号
US08080541B2

関連ノート

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