Methanol → 2-(4-chloro-3-(hydroxymethyl)pyridin-2-yl)-7,7-dimethyl-2,3,4,6,7,8-hexahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one

HRID 1021911ノート

反応式

HRID 1021911 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:19][CH2:18][N:17]3[C:10](=[CH:11][C:12]4[CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16]=43)[C:9]2=[O:22])[C:3]=1[CH:23]=[O:24].CO.[BH4-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:19][CH2:18][N:17]3[C:10](=[CH:11][C:12]4[CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16]=43)[C:9]2=[O:22])[C:3]=1[CH2:23][OH:24]

参加物

5

反応物 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 768540784-chloro-2-(7,7-dimethyl-1-oxo-1,3,4,6,7,8-hexahydro-2H-cyclopenta(4,5)pyrrolo(1,2-a)pyrazin-2-yl)nicotinaldehyde

生成物 1

HCID 866843692-(4-chloro-3-(hydroxymethyl)pyridin-2-yl)-7,7-dimethyl-2,3,4,6,7,8-hexahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one収率 77.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 4-chloro-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridine-3-carbaldehyde 108a (9.0 g, 26.1 mmol, 1.0 eq.), methanol (50 mL), dichloromethane (30 mL), and NaBH4 (5.95 g, 156.6 mmol, 5.0 eq.) at 0° C. The reaction mixture was stirred for 1 h. After the reaction was completed, the reaction was quenched with water and concentrated under reduced pressure. The residue was extracted with dichloromethane. The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 1:4 ethyl acetate/petroleum ether to afford 199c as a white solid (7.0 g, 77%). MS-ESI: [M+H]+ 345.9.

後処理

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customthe reaction was quenched with water
  3. concentrationconcentrated under reduced pressure
  4. extractionThe residue was extracted with dichloromethane
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica-gel column chromatography
  8. washeluting with 1:4 ethyl acetate/petroleum ether

出典と根拠

ORDレコード
ord-ed95975372dc41e284e207bf267e0634
出典データセット
uspto-grants-2014_05
特許番号
US08716274B2

反応ノート

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