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

HRID 1507672ノート

反応式

HRID 1507672 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

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)+

後処理

  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

出典と根拠

ORDレコード
ord-77d3f67b18c24bbbb40cb6af408abb5a
出典データセット
uspto-grants-2015_12
特許番号
US09221819B2

反応ノート

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