Formaldehyde → HCID 68338070、化合物

HRID 83004ノート

反応式

HRID 83004 の反応式
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O.[O:17]=[C:18]1[C:27]2([CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH2:26][C:25]2[C:20](=[N:21][CH:22]=[C:23](/[CH:33]=[CH:34]/[C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:24]=2)[NH:19]1.C(OCC)(=O)C>ClCCCl.O>[CH3:1][N:30]1[CH2:29][CH2:28][C:27]2([CH2:26][C:25]3[C:20](=[N:21][CH:22]=[C:23](/[CH:33]=[CH:34]/[C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:24]=3)[NH:19][C:18]2=[O:17])[CH2:32][CH2:31]1

参加物

7

反応物 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 68338146(E)-Ethyl 3-(2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4'-piperidine]-6-yl)acrylate

生成物 1

HCID 68338070HCID 68338070、化合物

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

Sodium triacetoxyborohydride (1.2 g, 5.73 mmol) and paraformaldehyde (172 mg, 5.73 mmol) were successively added to a suspension of (E)-ethyl 3-(2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-6-yl)acrylate (904 mg, 2.87 mmol) in 1,2-dichloroethane (40 mL) at room temperature. The reaction mixture was then heated up to 70° C. and stirred for 2 hours. After cooling down to room temperature, the reaction mixture was diluted by addition of ethyl acetate (50 mL) and water (50 mL). The aqueous layer was separated and extracted with ethyl acetate (2×50 mL). The combined organic phases were washed with a saturated solution of sodium hydrogenocarbonate (3×60 mL), dried over sodium sulfate, filtered and concentrated to dryness. The title product was obtained as a white solid (862 mg, 91%).

後処理

  1. temperatureAfter cooling down to room temperature
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. washThe combined organic phases were washed with a saturated solution of sodium hydrogenocarbonate (3×60 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-2ca92916a9bd45aabe9678e64824b521
出典データセット
uspto-grants-2014_09
特許番号
US08846711B2

反応ノート

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