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

HRID 1896116노트

반응식

HRID 1896116 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-30b8072800bd4714adde907f26bcc22a
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518933B2

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