Diethylamine → HCID 68828193、化合物

HRID 2099347ノート

反応式

HRID 2099347 の反応式
O=C(Cl)[O:3][C:4](Cl)(Cl)Cl.[CH:9]1([NH:15][CH:16]2[CH2:22][CH:21]3[N:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:18]([CH2:19][CH2:20]3)[CH2:17]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[CH2:31]([N:33](CC)[CH2:34][CH3:35])[CH3:32].C(NCC)C>ClCCl>[CH:9]1([N:15]([C:4]([N:33]([CH2:34][CH3:35])[CH2:31][CH3:32])=[O:3])[CH:16]2[CH2:17][CH:18]3[N:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:21]([CH2:20][CH2:19]3)[CH2:22]2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

参加物

6

反応物 4

HCID 8021DiethylamineHCID 8471Triethylamine2 回HCID 10426Diphosgene2 回HCID 68829044HCID 68829044、化合物

生成物 1

HCID 68828193HCID 68828193、化合物

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

0.64 ml of diphosgene is placed in 10 ml of dichloromethane at 0° C. under N2. A solution of 1.0 g of tert-butyl 3-(cyclohexylamino)-8-azabicyclo[3.2.1]-octane-8-carboxylate endo compound and 2.26 ml of triethylamine in 10 ml of dichloromethane is added dropwise. The solution is stirred at 0° C. for 30 min and then at ambient temperature for 4 h. 5 ml of triethylamine and 1.0 ml of diphosgene are then added. After stirring at ambient temperature for 2 h, 1.68 ml of diethylamine are added. The mixture is stirred at ambient temperature for 16 h. After concentration, 0.5N hydrochloric acid is added up to an acid pH. Extraction is carried out with dichloromethane until the aqueous phase is completely depleted. The organic phase is washed with H2O, and then with a saturated aqueous sodium chloride solution. After drying over MgSO4 and concentration to dryness, the residue obtained is chromatographed on silica gel, elution being carried out with a 99/1 and then 95/5 mixture of dichloromethane and methanol, to give 1.60 g of tert-butyl 3-{cyclohexyl[(diethylamino)carbonyl]amino}-8-azabicyclo[3.2.1]octane-8-carboxylate as a mixture with diethylurea.

後処理

  1. additionis added dropwise
  2. waitat ambient temperature for 4 h
  3. stirringAfter stirring at ambient temperature for 2 h
  4. stirringThe mixture is stirred at ambient temperature for 16 h
  5. concentrationAfter concentration, 0.5N hydrochloric acid
  6. additionis added up to an acid pH
  7. extractionExtraction
  8. washThe organic phase is washed with H2O
  9. dry with materialAfter drying over MgSO4 and concentration to dryness
  10. customthe residue obtained
  11. customis chromatographed on silica gel, elution
  12. addition95/5 mixture of dichloromethane and methanol

出典と根拠

ORDレコード
ord-765dac1cea6349ff9b799222c1b31a10
出典データセット
uspto-grants-2009_08
特許番号
US07569582B2

反応ノート

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