Hydrochloric Acid → Tert-butyl 1,2,4a,5,6,7-hexahydrobenzo[b]pyrazino[1,2-d][1,4]diazepine-3(4h)-carboxylate

HRID 1896116ノート

反応式

HRID 1896116 の反応式
O=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]2[CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH:4]2[CH2:3]1.B.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1.ClCCl.CO>[CH2:13]1[N:5]2[C:6]3[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=3[NH:8][CH2:2][CH2:3][CH:4]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 516892Sodium BicarbonateHCID 58284919tert-butyl 6-oxo-1,2,4a,5,6,7-hexahydropyrazino[1,2-a][1,5]benzodiazepine-3(4H)-carboxylate

生成物 1

HCID 58284934Tert-butyl 1,2,4a,5,6,7-hexahydrobenzo[b]pyrazino[1,2-d][1,4]diazepine-3(4h)-carboxylate

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a solution of Example 1C (1 g, 3.15 mmol) in tetrahydrofuran (10 mL) was added borane (1 M/tetrahydrofuran, 12.6 mL, 12.6 mmol). The solution was heated to 80° C. for 4 hours. Methanol (20 mL) was added, and the reaction heated at 80° C. for 1 hour. The reaction was cooled to room temperature and 1 M HCl (30 mL) was added. This solution was stirred for 30 minutes, before the solution was neutralized with sodium bicarbonate (aqueous). Dichloromethane was used to extract the product. The product was purified via flash chromatography (20-70% ethyl acetate/hexanes) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 6.77 (d, J=7.54 Hz, 1 H), 6.64-6.73 (m, 1 H), 6.48-6.59 (m, 2 H), 5.27 (s, 1 H), 3.54-3.67 (m, 1 H), 3.35-3.50 (m, 2 H), 3.20-3.29 (m, 1 H), 2.96-3.19 (m, 4 H), 2.85-2.96 (m, 1 H), 1.76-1.92 (m, 1 H), 1.59-1.75 (m, 1 H), 1.41 (s, 9 H); MS (APCI+) m/z 304.3 (M+H)+.

後処理

  1. temperaturethe reaction heated at 80° C. for 1 hour
  2. temperatureThe reaction was cooled to room temperature
  3. extractionto extract the product
  4. customThe product was purified via flash chromatography (20-70% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-30b8072800bd4714adde907f26bcc22a
出典データセット
uspto-grants-2013_08
特許番号
US08518933B2

反応ノート

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