Lithium borohydride → N-(1,3-Dihydroxy-2-(6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl)propan-2-yl)acetamide

HRID 1921687ノート

反応式

HRID 1921687 の反応式
[BH4-].[Li+].C([O:5][C:6](=O)[C:7]([NH:31][C:32](=[O:34])[CH3:33])([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)[CH2:14]1)[C:8](OCC)=[O:9])C>C1COCC1.C(OCC)(=O)C>[OH:9][CH2:8][C:7]([NH:31][C:32](=[O:34])[CH3:33])([CH2:6][OH:5])[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)[CH2:14]1

参加物

5

反応物 2

HCID 4148881Lithium borohydrideHCID 57577378Diethyl 2-acetamido-2-(6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl)malonate

生成物 1

HCID 57577382N-(1,3-Dihydroxy-2-(6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl)propan-2-yl)acetamide収率 33%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Lithium borohydride (2M solution in THF, 0.88 ml, 1.76 mmol) was added to compound 6 (200 mg, 0.44 mmol) in 5 ml THF at 0° C. The reaction mixture was stirred at room temperature for 48 hours and diluted with 40 ml ethyl acetate. The solution was washed with brine (2×20 mL) and dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography (Silica gel, 4% MeOH in CH2Cl2) to provide 55 of mg compound 7 (33%).

後処理

  1. washThe solution was washed with brine (2×20 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by column chromatography (Silica gel, 4% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-03f214d8cbb544d98c3f5607c87e6bc1
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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