Acetic Acid → HCID 86669247、化合物

HRID 2366909ノート

反応式

HRID 2366909 の反応式
[CH3:1][CH:2]([O:4][C:5](=[O:28])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]3[O:18][CH:19]=[C:20]([CH:22]=O)[CH:21]=3)[CH:15]=2)[N:10]([C:24](=[O:26])[CH3:25])[C@@H:9]([CH3:27])[CH2:8]1)[CH3:3].[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:24]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([C:17]3[O:18][CH:19]=[C:20]([CH2:22][N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[CH:21]=3)=[CH:13][CH:12]=2)[C@H:7]([NH:6][C:5](=[O:28])[O:4][CH:2]([CH3:3])[CH3:1])[CH2:8][C@@H:9]1[CH3:27])(=[O:26])[CH3:25]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86669230HCID 86669230、化合物

生成物 1

HCID 86669247HCID 86669247、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1-Methylethyl[(cis)-1-acetyl-6-(4-formyl-2-furanyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 20) (28 mg, 0.073 mmol) was dissolved in dichloromethane (DCM) (1 mL), mixed with piperidine (8.65 μL, 0.087 mmol) and acetic acid (8.34 μL, 0.146 mmol) and stirred under nitrogen for 30 minutes. Sodium triacetoxyborohydride (20.07 mg, 0.095 mmol) was added and the mixture was stirred again under nitrogen. After 16 hours reaction time the mixture was loaded onto a 2 g Flash SCX-column, eluting with MeOH (60 mL) followed by 2M MeOH/NH3 (60 mL). The product-containing fraction was evaporated to dryness to give a light brown solid (19 mg).

後処理

  1. stirringthe mixture was stirred again under nitrogen
  2. customAfter 16 hours reaction time the mixture
  3. washeluting with MeOH (60 mL)
  4. customThe product-containing fraction was evaporated to dryness

出典と根拠

ORDレコード
ord-9262b3e6abe44d3aa6f921bab622d71b
出典データセット
uspto-grants-2014_04
特許番号
US08697725B2

反応ノート

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