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Sodium borohydride → HCID 13799992, 화합물

HRID 475286
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HRID 475286 반응식
[S:1]([N:11]1[C:19]2[C:14](=[C:15]([C:20](=[O:22])[CH3:21])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[BH4-].[Na+]>CO>[S:1]([N:11]1[C:19]2[C:14](=[C:15]([CH:20]([OH:22])[CH3:21])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]
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참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 71272214HCID 71272214, 화합물

생성물 1

HCID 13799992HCID 13799992, 화합물수율 95.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of 1-(1-tosyl-1H-indol-4-yl)ethanone (500 mg, 1.4 mmol, CASRN 112970-73-7) in dry MeOH (5 mL) at 0° C. was added NaBH4 (80 mg, 2.1 mmol) and the mixture was stirred at RT overnight. The mixture was concentrated in vacuo and the residue was diluted with EtOAc, washed sequentially with water and brine. The organics were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography to afford 420 mg (95%) of 1-(1-tosyl-1H-indol-4-yl)ethanol (282) as white semi-solid: 1H NMR (400 MHz, DMSO-d6) δ 7.85 (d, J=8.4 Hz, 2H), 7.81-7.76 (m, 2H), 7.37 (d, J=8.0 Hz, 2H), 7.31-7.23 (m, 2H), 6.98 (d, J=3.6 Hz, 1H), 5.23 (d, J=4 Hz, 1H), 5.04-5.01 (m, 1H), 2.30 (s, 3H), 1.33 (d, J=6.4 Hz, 3H).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was diluted with EtOAc
  3. washwashed sequentially with water and brine
  4. dry with materialThe organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by SiO2 chromatography

출처 및 근거

ORD 기록
ord-6226d9d84931434f84cc1dafc2849e55
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08637537B2

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