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

HRID 356201

反応式

HRID 356201 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 6451Bromocresol Green触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0a8b08a493824814808e84cd6b43072d
出典データセット
uspto-grants-1998_11
特許番号
US05834463

関連ノート

読み込み中…