Sodium borohydride → HCID 57577369、化合物

HRID 1921691ノート

反応式

HRID 1921691 の反応式
[BH4-].[Na+].[CH2:3]([O:5][C:6](=[O:36])[C:7]([NH:32][C:33](=[O:35])[CH3:34])([CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:19]=2)[C:14]1=[O:31])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]>C(O)C>[CH2:3]([O:5][C:6](=[O:36])[C:7]([NH:32][C:33](=[O:35])[CH3:34])([CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:19]=2)[CH:14]1[OH:31])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 57577370Diethyl acetamido(6-octyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propanedioate2 回

生成物 1

HCID 57577369HCID 57577369、化合物収率 75.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

To a solution of sodium borohydride (75 mg, 2.00 mmol) in 5 ml of ethanol at room temperature is added 2-acetylamino-2-(6-octyl-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-malonic acid diethyl ester (compound 5) (1.00 g, 2.1 mmol) in 5 ml of ethanol. The reaction mixture is stirred at room temperature under argon for an additional hour, quenched by the addition of water (20 mL) and methylene chloride (20 mL). The organic layer is removed and the aqueous layer is extracted with methylene chloride (2×20 mL). The combined organic layers were washed with brine (2×20 mL) and dried over magnesium sulfate and concentrated under vacuum. The residue is purified by column chromatography (silica gel, 20% ethyl acetate in hexanes) to provide 755 mg of compound A (75%).

後処理

  1. customquenched by the addition of water (20 mL) and methylene chloride (20 mL)
  2. customThe organic layer is removed
  3. extractionthe aqueous layer is extracted with methylene chloride (2×20 mL)
  4. washThe combined organic layers were washed with brine (2×20 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by column chromatography (silica gel, 20% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-32b0801000f94920870d7ca21932cfb3
出典データセット
uspto-grants-2012_05
特許番号
US08173710B2

反応ノート

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