Sodium bis(2-methoxyethoxy)aluminiumhydride → (S)-5,11-Dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]-thiazepine

HRID 1460487노트

반응식

HRID 1460487 반응식
[H-].COCCO[Al+]OCCOC.[Na+].[H-].CC1C=CC(S([N:25]2[CH2:29][CH2:28][CH2:27][C@H:26]2[CH2:30][N:31]2[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=3[CH2:35][S:34][C:33]3[CH:42]=[CH:43][CH:44]=[CH:45][C:32]2=3)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[NH:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[CH2:30][N:31]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[CH2:35][S:34][C:33]2[CH:42]=[CH:43][CH:44]=[CH:45][C:32]1=2

참가 물질

4

반응물 2

HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 22841645(S)-5,11-Dihydro-5-(1-[4-methylphenylsulphonyl]-2-pyrrolidinylmethyl)dibenzo[b,e][1,4]thiazepine

생성물 1

HCID 22841647(S)-5,11-Dihydro-5-(2-pyrrolidinylmethyl)dibenzo[b,e][1,4]-thiazepine수율 55.1%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

Sodium bis(2-methoxyethoxy)aluminium hydride ("Red-Al"-registered Trade Mark) (20.8 ml of a 3.4M solution in toluene) was added to a solution of (S)-5,11-dihydro-5-(1-[4-methylphenylsulphonyl]-2-pyrrolidinylmethyl)dibenzo[b,e][1,4]thiazepine (see Preparations 15 and 16) (8.0 g) in toluene (50 ml) and the mixture heated under reflux for 27 hours, allowed to cool to room temperature, quenched by the addition of 2.5M aqueous sodium hydroxide solution, diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel, performing a gradient elution initially using dichloromethane as eluant and changing to dichloromethane/saturated methanolic ammonia (90:10). Appropriate fractions were combined and evaporated under reduced pressure to give the title compound as a colourless oil, (2.9 g, 55%), [α]589 -4.9° (c=1.065 in ethanol).

후처리

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 27 hours
  3. customquenched by the addition of 2.5M aqueous sodium hydroxide solution
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. customevaporated under reduced pressure
  9. customThe residue was purified by chromatography on silica gel
  10. washa gradient elution initially using dichloromethane as eluant
  11. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-38e002976d0d408f98629c5d4ce871c2
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05071844

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