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

HRID 356201

반응식

HRID 356201 반응식
[CH2:1]1[CH:10]2[C:4](=[N:5][C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][C:9]2=[O:11])[CH2:3][CH2:2]1.C([BH3-])#N.[Na+].Cl.CO.C(=O)([O-])O.[Na+]>CO.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]1[CH:10]2[CH:4]([NH:5][C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][C:9]2=[O:11])[CH2:3][CH2:2]1

참가 물질

9

반응물 4

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 123949352,3,9,10a-Tetrahydro-1H-benzo[b]cyclopenta[f][1,4]diazepin-10-oneHCID 21893726Hydrochloride methanol

생성물 1

HCID 189405902,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one수율 100,187.5%

시약·촉매·용매 4

HCID 6451Bromocresol Green촉매HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

2,3,9,10a-Tetrahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-one (38.3 g, 0.19 mmol) and bromocresol green (30 mg) were suspended in a mixture of methanol (200 mL) and tetrahydrofuran (200 mL), which was cooled to 0° C. To the suspension was added, at the same temperature, sodium cyanoborohydride (13.2 g, 0.21 mmol), to which was then added dropwise gradually a 10% hydrogen chloride-methanol solution until no more color change of the reaction system was observed. To the reaction mixture was added water (500 mL), which was made alkaline with a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with chloroform three times. Organic layers were combined, washed with water and a saturated aqueous solution of sodium chloride, dried over sodium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure to give 38.5 g (yield 99%) of the titled compound. The sample for analytical use was prepared by recrystallization from ethanol as a cis-trans mixture (1:1). m.p. 191°-212° C.

후처리

  1. extractionfollowed by extraction with chloroform three times
  2. washwashed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulfate
  4. filtrationsubjected to filtration
  5. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0a8b08a493824814808e84cd6b43072d
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834463

연결된 노트

불러오는 중…