Water → (7R)-benzyl 2,4-dioxo-1,3-diazaspiro[4.4]nonane-7-carboxylate

HRID 1507672노트

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HRID 1507672 반응식
O=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[C-:17]#[N:18].[Na+].[C:20](=[O:23])([O-])[O-].[NH4+:24].[NH4+].[OH2:26]>C(O)C>[O:26]=[C:17]1[NH:24][C:20](=[O:23])[C:2]2([CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:8])[CH2:3]2)[NH:18]1

참가 물질

6

반응물 4

HCID 962WaterHCID 8929Sodium CyanideHCID 517111Ammonium CarbonateHCID 86668857(R)-benzyl 3-oxocyclopentanecarboxylate

생성물 1

HCID 68179167(7R)-benzyl 2,4-dioxo-1,3-diazaspiro[4.4]nonane-7-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
70 °C

실험 절차

To (R)-benzyl 3-oxocyclopentanecarboxylate (0.5 g, 2.291 mmol) in ethanol (5 mL) were sequentially added sodium cyanide (0.281 g, 5.73 mmol), ammonium carbonate (2.86 g, 29.8 mmol) and water (5.00 mL) at room temperature. The contents were heated at 70° C. (oil bath temp.) for 3 hours. The reaction mixture was kept at room temperature for 10 min. Solid separates out. The solid was filtered and washed with water (3×10 mL). The solid was dried overnight under vacuum (155 mg, 0.538 mmol, 23.5%) and used as such for the subsequent step without further purification. MS (ESI) m/z 289.16 (M+H)+

후처리

  1. customat room temperature
  2. filtrationThe solid was filtered
  3. washwashed with water (3×10 mL)
  4. customThe solid was dried overnight under vacuum (155 mg, 0.538 mmol, 23.5%)
  5. customwithout further purification

출처 및 근거

ORD 기록
ord-77d3f67b18c24bbbb40cb6af408abb5a
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221819B2

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