4-Heptanone → 1-[2-(4-Heptylamino)-4-methoxycarbonylphenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-one

HRID 1635561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1635561
[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][CH2:24][C:25](=O)[CH2:26][CH2:27][CH3:28].C([BH3-])#N.[Na+]>ClCCl.C(O)(=O)C>[CH3:22][CH2:23][CH2:24][CH:25]([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])[CH2:26][CH2:27][CH3:28]

Komponenten

6

Edukt 3

HCID 312464-Heptanone2×HCID 5003444Sodium cyanoborohydride2×HCID 105657101-(2-Amino-4-methoxycarbonylphenyl)-5,5-bis-hydroxymethylpyrrolidin-2-one

Produkt 1

HCID 120183111-[2-(4-Heptylamino)-4-methoxycarbonylphenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-oneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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 0.3 mL of acetic acid was treated with 4-heptanone (0.175 g, 1.53 mmol) and sodium cyanoborohydride (0.05 g, 0.8 mmol). The resulting mixture was stirred at ambient temperature for 12 h after which time addition 4-heptanone (0.175 g, 1.53 mmol), sodium cyanoborohydride (0.05 g, 0.8 mmol) and acetic acid (0.3 mL) were added. Stirring was continued for 12 h. The reaction mixture was quenched with 10 mL of a saturated sodium bicarbonate solution and the mixture was extracted with ethyl acetic (3×50 mL). The combined extracts were dried and concentrated. The residue was purified by chromatography (silica gel; 5% ethanol in ether) to give 0.15 g (75%) of 1-[2-(4-heptylamino)-4-methoxycarbonylphenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-one as a white solid, mp 139-140° C.

Aufarbeitung

  1. additionwere added
  2. stirringStirring
  3. waitwas continued for 12 h
  4. customThe reaction mixture was quenched with 10 mL of a saturated sodium bicarbonate solution
  5. extractionthe mixture was extracted with ethyl acetic (3×50 mL)
  6. customThe combined extracts were dried
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (silica gel; 5% ethanol in ether)

Quellen und Nachweise

ORD-Eintrag
ord-80d5cc46550b469e91c51377fdfebf13
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06509359B1

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