Sodium borohydride → tert-Butyl 6-(hydroxymethyl)-1H-indole-1-carboxylate

HRID 551500ノート

反応式

HRID 551500 の反応式
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=[O:18])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][OH:18])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 14616867Tert-butyl 6-formyl-1H-indole-1-carboxylate

生成物 1

HCID 23560816tert-Butyl 6-(hydroxymethyl)-1H-indole-1-carboxylate収率 78%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 6-formyl-indole-1-carboxylic acid tert-butyl ester (1.2 g) in methanol (5 mL) in an ice bath was added sodium borohydride (0.27 mg) portion wise. The reaction was allowed to warm to room temperature over 1.5 hr. The reaction diluted with ethyl acetate (200 mL) washed with water (200 mL), brine (100 mL), dried over sodium sulfate, concentrated, adsorbed onto silica gel and purified by flash chromatography with a gradient from 5-40% ethyl acetate in hexanes to yield 6-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester as a clear viscous oil (0.91 g, 78%) LC-MS (ES) calculated for C14H17NO3, 247.1; found m/z 246 [M−H]−.

後処理

  1. washwashed with water (200 mL), brine (100 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by flash chromatography with a gradient from 5-40% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-9a2b0b784e274660a39d5f4ea3df2cd7
出典データセット
uspto-grants-2011_05
特許番号
US07947728B1

反応ノート

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