Sodium borohydride → 2-(2,5-Dimethyl-1H-pyrrol-1-yl)-4-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

HRID 1412005ノート

反応式

HRID 1412005 の反応式
[CH3:1][C:2]1[N:3]([C:8]2[CH:17]=[C:11]3[C:12]([CH3:16])=[N:13][CH2:14][CH2:15][N:10]3[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[BH4-].[Na+]>CO>[CH3:7][C:4]1[N:3]([C:8]2[CH:17]=[C:11]3[CH:12]([CH3:16])[NH:13][CH2:14][CH2:15][N:10]3[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 866845252-(2,5-Dimethyl-1H-pyrrol-1-yl)-4-methyl-6,7-dihydropyrazolo[1,5-a]pyrazine

生成物 1

HCID 866845262-(2,5-Dimethyl-1H-pyrrol-1-yl)-4-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine収率 43%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 287f (3.56 g, 1.0 eq., 15.6 mmol), NaBH4 (2.96 g, 5.0 eq., 78.0 mmol), and methanol (50 mL). The mixture was stirred at room temperature for 1 h and concentrated under reduced pressure. The residue was partitioned between water (50 mL) and dichloromethane (50 mL). The water phase was extracted with dichloromethane (3×50 mL). The combined organic layer was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 10:1 dichloromethane/methanol to afford 287g as a colorless oil (1.54 g, 43% over two steps). MS-ESI: [M+H]+ 231.3. 1H NMR (500 MHz, CDCl3) δ 5.91 (s, 1H), 5.86 (s, 2H), 4.17-4.11 (m, 3H), 3.51-3.48 (m, 1H), 3.36-3.31 (m, 1H), 2.13 (s, 6H), 1.50 (d, J=6.5 Hz, 3H).

後処理

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between water (50 mL) and dichloromethane (50 mL)
  4. extractionThe water phase was extracted with dichloromethane (3×50 mL)
  5. concentrationThe combined organic layer was concentrated under reduced pressure
  6. customThe residue was purified by silica-gel column chromatography
  7. washeluting with 10:1 dichloromethane/methanol

出典と根拠

ORDレコード
ord-8001de65769d4adb92037a0d33cf5975
出典データセット
uspto-grants-2014_12
特許番号
US08921353B2

反応ノート

読み込み中…