Formaldehyde → HCID 45117639、化合物

HRID 1057166

反応式

HRID 1057166 の反応式
[C:1]([BH3-])#N.[Na+].Cl.[S:6]1[C:14]2[CH2:13][CH2:12][NH:11][CH2:10][C:9]=2[CH:8]=[CH:7]1.C=O>ClCCl>[CH3:1][N:11]1[CH2:12][CH2:13][C:14]2[S:6][CH:7]=[CH:8][C:9]=2[CH2:10]1

参加物

5

反応物 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 101763424,5,6,7-Tetrahydrothieno(3,2-c)pyridinium chloride

生成物 1

HCID 45117639HCID 45117639、化合物収率 33%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Sodium cyanoborohydride (10 g, 160 mmol) was slowly added to a mixture of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (7.0 g, 40.0 mmol) and formaldehyde (35% in water, 10 mL) in dichloromethane (100 mL) at room temperature. The resulting mixture was stirred at room temperature for 16 h. Work-up: the reaction mixture was partitioned between ethyl acetate (300 mL) and water (200 mL). The organic layer was separated, washed with brine (100 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc/petroleum ether=1:5˜1:1) to afford the title compound as a white solids (2.0 g, 33%). 1H NMR (DMSO-d6, 400 MHz): δ 7.26 (d, 1H), 6.77 (d, 1H), 3.37 (s, 2H), 2.80-2.77 (m, 2H), 2.64-2.60 (m, 2H), 2.34 (s, 3H).

後処理

  1. customthe reaction mixture was partitioned between ethyl acetate (300 mL) and water (200 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (EtOAc/petroleum ether=1:5˜1:1)

出典と根拠

ORDレコード
ord-a44775a76b5d412ebcf6c2f5b4c94991
出典データセット
uspto-grants-2016_07
特許番号
US09399646B2

関連ノート

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