Formaldehyde → HCID 68338070、化合物

HRID 634036ノート

反応式

HRID 634036 の反応式
[O:1]=[C:2]1[C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:10][C:9]2[C:4](=[N:5][CH:6]=[C:7](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=2)[NH:3]1.[C:24](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>ClCCCl>[CH3:24][N:14]1[CH2:13][CH2:12][C:11]2([CH2:10][C:9]3[C:4](=[N:5][CH:6]=[C:7](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=3)[NH:3][C:2]2=[O:1])[CH2:16][CH2:15]1

参加物

5

反応物 3

HCID 712FormaldehydeHCID 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 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
70 °C

実験手順

To a suspension of (E)-ethyl 3-(2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-6-yl)acrylate (99.8 mg, 0.316 mmol) in 1,2-dichloroethane (5 mL) were added sodium triacetoxyborohydride (139 mg, 0.656 mmol) and paraformaldehyde (21 mg, 0.699 mmol). The reaction mixture was heated to 70° C. for 5 h. After cooling to room temperature, the reaction mixture was partitioned between DCM (25 mL) and water (25 mL). The aqueous layer was separated and extracted with DCM (2×20 mL). The combined organic phases were washed with saturated NaHCO3 (3×25 mL) and brine (25 mL), dried over sodium sulfate and concentrated. The crude product was used directly in the next step.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between DCM (25 mL) and water (25 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with DCM (2×20 mL)
  5. washThe combined organic phases were washed with saturated NaHCO3 (3×25 mL) and brine (25 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-f3aff27617b94a17bea5d4561c1033f3
出典データセット
uspto-grants-2016_04
特許番号
US09321769B2

反応ノート

読み込み中…