Sodium Bicarbonate → 9-Benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 356148

반응식

HRID 356148 반응식
[CH2:1]([N:8]1[C:14](=[O:15])[CH:13]2[CH2:16][CH2:17][CH2:18][C:12]2=[N:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].Cl.C(O)C.C(=O)([O-])O.[Na+]>C(O)C.O1CCCC1.CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.O>[CH2:1]([N:8]1[C:14](=[O:15])[CH:13]2[CH2:16][CH2:17][CH2:18][CH:12]2[NH:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

9

반응물 4

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 21887872Ethanol hydrochlorideHCID 530333449-benzyl-2,3,9,10a-tetrahydrocyclopenta[b][1,5]benzodiazepin-10(1H)-one

생성물 1

HCID 701097929-Benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one수율 83.5%

시약·촉매·용매 4

HCID 6451Bromocresol Green촉매HCID 702Ethanol용매2회HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A suspension of 9-benzyl-2,3,9,10a-tetrahydrobenzo [b]cyclopenta[e][1,4]diazepin-10(1H)-one (87.5 g, 0.30 mol) and bromocresol green (20 mg) in ethanol (300 mL) in a mixture of ethanol (300 mL) and tetrahydrofuran (300 mL) was cooled to 0° C., to which was added sodium cyanoborohydride (20.8 g, 0.33 mol). To the mixture was added dropwise slowly a 2.43N HCl-ethanol solution until the color of the solution does not change any more. To the reaction mixture was added water (800 mL), to which was added a saturated aqueous solution of sodium hydrogencarbonate to make the pH of the solution alkaline. Resulting crystalline precipitate was collected by filtratin, washed with water, and dried at 60° C. over diphosphorus pentoxide under reduced pressure to give 73.2 g (yield 83%) of the titled compound. The filtrate was concentrated under reduced pressure to distill off the organic solvent. The aqueous layer was subjected to extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was recrystallized from ethyl acetate-hexane to give additional 7.0 g (7%) of the titled compound, m.p. 172°-173° C.

후처리

  1. customResulting crystalline precipitate was collected by filtratin
  2. washwashed with water
  3. dry with materialdried at 60° C. over diphosphorus pentoxide under reduced pressure

출처 및 근거

ORD 기록
ord-acfc87706d1e40879a84a95d64d622f1
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834463

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