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

HRID 356148

反応式

HRID 356148 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 6451Bromocresol Green触媒HCID 702Ethanol溶媒2 回HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-acfc87706d1e40879a84a95d64d622f1
出典データセット
uspto-grants-1998_11
特許番号
US05834463

関連ノート

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