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

HRID 1950895

반응식

HRID 1950895 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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)+].

후처리

  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)

출처 및 근거

ORD 기록
ord-5e0e1221301f4894b1529479b925d73b
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404673B2

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