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

HRID 1635561ノート

反応式

HRID 1635561 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-80d5cc46550b469e91c51377fdfebf13
出典データセット
uspto-grants-2003_01
特許番号
US06509359B1

反応ノート

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