Methanol → 1-[2-(3-Hexylamino)-4-methoxycarbonylphenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-one

HRID 1635560노트

반응식

HRID 1635560 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[C:16]([CH2:19][OH:20])([CH2:17][OH:18])[CH2:15][CH2:14][C:13]1=[O:21].[CH3:22][CH2:23][C:24](=O)[CH2:25][CH2:26][CH3:27].C([BH3-])#N.[Na+].CO>ClCCl.C(O)(=O)C>[CH3:22][CH2:23][CH:24]([NH:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[C:16]([CH2:17][OH:18])([CH2:19][OH:20])[CH2:15][CH2:14][C:13]1=[O:21])[CH2:25][CH2:26][CH3:27]

참가 물질

7

반응물 4

HCID 887MethanolHCID 115093-Hexanone3회HCID 5003444Sodium cyanoborohydride3회HCID 105657101-(2-Amino-4-methoxycarbonylphenyl)-5,5-bis-hydroxymethylpyrrolidin-2-one

생성물 1

HCID 120183091-[2-(3-Hexylamino)-4-methoxycarbonylphenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-one수율 90.7%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

A solution of 1-(2-amino-4-methoxycarbonylphenyl)-5,5-bis-(hydroxymethyl)pyrrolidin-2-one (0.15 g, 0.51 mmol) from Example 6 in 1 mL of dichloromethane and 0.5 mL of acetic acid was treated with 3-hexanone (0.3 g, 3 mmol) and sodium cyanoborohydride (0.1 g, 1.6 mmol). The resulting mixture was stirred at ambient temperature for 6 h after which time additional 3-hexanone (0.1 g, 1 mmol), sodium cyanoborohydride (0.05 g, 0.8 mmol) and methanol (0.5 mL) were added. Stirring was continued for 12 h. A third portion of 3-hexanone (0.17 g, 1.7 mmol) and sodium cyanoborohydride (0.055 g, 0.9 mmol) was added and stirring continued for an additional 16 h. The reaction mixture was quenched with 10 mL of a saturated sodium bicarbonate solution and extracted with ethyl acetate (3×50 mL). The combined extracts were dried and concentrated. The residue was purified by chromatography (silica gel; 5% ethanol in ether) to give 0.175 g (90%) of 1-[2-(3-hexylamino)-4-methoxycarbonylphenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-one as an oil.

후처리

  1. additionwere added
  2. stirringstirring
  3. waitcontinued for an additional 16 h
  4. customThe reaction mixture was quenched with 10 mL of a saturated sodium bicarbonate solution
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. customThe combined extracts were dried
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (silica gel; 5% ethanol in ether)

출처 및 근거

ORD 기록
ord-0e928ae78d3b4d7eb107ce2b6c327463
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06509359B1

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