Sodium triacetoxyborohydride → HCID 71112545、化合物

HRID 1472757ノート

反応式

HRID 1472757 の反応式
[OH:1][C:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:4].[O:25]1[CH2:29][CH2:28][O:27][CH:26]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36]1[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][CH:37]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[OH:1][C:2]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:3]([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:40][C:39]2[CH:38]=[CH:37][C:36]([O:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH:26]3[O:25][CH2:29][CH2:28][O:27]3)=[CH:43][CH:42]=2)[CH2:9][CH2:8]1)=[O:4]

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 71093464HCID 71093464、化合物HCID 86676461HCID 86676461、化合物

生成物 1

HCID 71112545HCID 71112545、化合物収率 70.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of piperidin-4-ylmethyl 2-hydroxy-2,2-diphenylacetate (0.4 g, 1.23 mmol) and 4-((5-(1,3-dioxolan-2-yl)pentyl)oxy)benzaldehyde (0.38 g, 1.44 mmol) in DCM (5 mL) was added sodium triacetoxyborohydride (0.388 g, 1.83 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between EtOAc and saturated sodium hydrogen carbonate. The organic phase was dried (sodium sulfate), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with 1 to 10% methanol in ethyl acetate to afford the title compound as a colourless oil (0.50 g, 26%).

後処理

  1. customThe reaction mixture was partitioned between EtOAc and saturated sodium hydrogen carbonate
  2. dry with materialThe organic phase was dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by silica gel column chromatography
  6. washeluting with 1 to 10% methanol in ethyl acetate

出典と根拠

ORDレコード
ord-fdff5b2b358b44d0a060dcbea15e4be6
出典データセット
uspto-grants-2015_04
特許番号
US09012644B2

反応ノート

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