Sodium hydride → 4-t-Butoxycarbonyl-2-[2-(4-phenylbutyl)phenoxymethyl]morpholine

HRID 743181노트

반응식

HRID 743181 반응식
[H-].[Na+].[C:3]1([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][O:30][CH:29]([CH2:33]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>CC(N(C)C)=O>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][O:30][CH:29]([CH2:33][O:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][CH2:10][CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 125964892-(4-Phenylbutyl)phenolHCID 19423893N-BOC-2-(tosyloxymethyl)morpholine

생성물 1

HCID 106936854-t-Butoxycarbonyl-2-[2-(4-phenylbutyl)phenoxymethyl]morpholine수율 31.6%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

218 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling and stirring, to a solution of 1.13 g of 2-(4-phenylbutyl)phenol (prepared as described in Preparation 3) in 20 ml of dimethylacetamide, and the resulting mixture was stirred at room temperature for 30 minutes. At the end of this time, 2.04 g of 4-t-butoxycarbonyl-2-(p-toluenesulfonyloxymethyl)morpholine were added, and the reaction mixture was stirred at 60° C. for 6 hours. The mixture was then partitioned between ethyl acetate and water. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The oily residue thus obtained was purified by column chromatography through silica gel, using a 20:1 by volume mixture of benzene and acetonitrile as the eluent, to give 671 mg of the title compound as an oil.

후처리

  1. temperaturecooling
  2. stirringthe reaction mixture was stirred at 60° C. for 6 hours
  3. customThe mixture was then partitioned between ethyl acetate and water
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe oily residue thus obtained
  8. customwas purified by column chromatography through silica gel
  9. additionby volume mixture of benzene and acetonitrile as the eluent

출처 및 근거

ORD 기록
ord-cd00c680ccce442eb88feaaba99b697d
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556864

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