Methanol → 1-[4-Methoxycarbonyl-2-(3-pentylamino)phenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-one

HRID 1635558노트

반응식

HRID 1635558 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][CH3:26].C([BH3-])#N.[Na+].CO>ClCCl.C(O)(=O)C>[CH3:11][O:10][C:8]([C:6]1[CH:5]=[CH:4][C:3]([N:12]2[C:16]([CH2:17][OH:18])([CH2:19][OH:20])[CH2:15][CH2:14][C:13]2=[O:21])=[C:2]([NH:1][CH:24]([CH2:25][CH3:26])[CH2:23][CH3:22])[CH:7]=1)=[O:9]

참가 물질

7

반응물 4

HCID 887MethanolHCID 7288Ethyl ketone3회HCID 5003444Sodium cyanoborohydride3회HCID 105657101-(2-Amino-4-methoxycarbonylphenyl)-5,5-bis-hydroxymethylpyrrolidin-2-one

생성물 1

HCID 104990031-[4-Methoxycarbonyl-2-(3-pentylamino)phenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-one수율 84.7%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

A solution of 1-(2-amino-4-methoxycarbonylphenyl)-5,5-bis-hydroxymethylpyrrolidin-2-one (0.1 g, 0.34 mmol) from Example 6 in 1 mL of dichloromethane and 0.5 mL of acetic acid was treated with 3-pentanone (0.2 g, 2.3 mmol) and sodium cyanoborohydride (0.075 g, 1.2 mmol). The resulting mixture was stirred at ambient temperature for 6 h after which time additional 3-pentanone (0.2 g, 2.3 mmol), sodium cyanoborohydride (0.075 g, 1.2 mmol) and methanol (0.5 mL) were added and stirring continued for 12 h. A third portion of 3-pentanone (0.3. g, 3.4 mmol) and sodium cyanoborohydride (0.15 g, 2.3 mmol) was added and the stirring continued for an additional 16 h. The reaction mixture was quenched with 10 mL of a saturated sodium bicarbonate solution, and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried and concentrated. The residue was purified by chromatography (silica gel; 5% ethanol in ether) to give 0.105 g (82%) of 1-[4-methoxycarbonyl-2-(3-pentylamino)phenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-one as a white solid, mp 183-185° C.

후처리

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

출처 및 근거

ORD 기록
ord-45f644c746fb4882af52953c6ae6bad2
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06509359B1

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