Acetic Acid → 78867-61-5

HRID 986921

反応式

HRID 986921 の反応式
[CH2:1]1[C@H:6]2[C:7]3[N:13]([CH2:14][C@@H:2]1[CH2:3][NH:4][CH2:5]2)[C:11](=[O:12])[CH:10]=[CH:9][CH:8]=3.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]1[C@H:6]2[C:7]3[N:13]([CH2:14][C@@H:2]1[CH2:3][N:4]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:5]2)[C:11](=[O:12])[CH:10]=[CH:9][CH:8]=3

参加物

6

反応物 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 10235CytisineHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 87291278867-61-5収率 58%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a 25 ml round bottom flask was added 0.510 gm (2.68 mmol) cytisine in 10 ml of 1,2-dichloroethane. The above solution was treated with 0.272 ml (2.68 mmol) benzaldehyde, 153 μl acetic acid and 0.852 gm (4.02 mmol) sodium triacetoxyborohydride. The reaction mixture was stirred at room temperature for 2 hours and was then partitioned between methylene chloride 1 N HCl (aq). The organic phase was washed with brine, dried and the solvent evaporated in vacuo to a solid. Chromatography on silica gel eluting with 1% methanol in methylene chloride afforded 434 mg (58%) of the title product which was used in the next step. 1H NMR (CDCl3, 250 MHz) δ7.28 (dd, 1H), 7.15 (m, 3H), 6.98 (m, 2H), 6.52 (d, 1H), 5.92 (d, 1H), 4.10 (d, 1H), 3.88 (dd, 1H), 3.40 (dd, 2H), 2.88 (m 3H), 2.39 (brs, 1H), 2.32 (dd, 2H), 1.82 (dd, 2H) ppm.

後処理

  1. customwas then partitioned between methylene chloride 1 N HCl (aq)
  2. washThe organic phase was washed with brine
  3. customdried
  4. customthe solvent evaporated in vacuo to a solid

出典と根拠

ORDレコード
ord-cdad4cd2fa6843b5ad294d5cb3bf27f9
出典データセット
uspto-grants-2003_10
特許番号
US06630467B2

関連ノート

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