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

HRID 551500노트

반응식

HRID 551500 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

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]−.

후처리

  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

출처 및 근거

ORD 기록
ord-9a2b0b784e274660a39d5f4ea3df2cd7
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947728B1

반응 노트

불러오는 중…