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Sodium Carbonate → 2-(benzyloxy)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one

HRID 1396510
ノート
印刷プレビュー

反応式

HRID 1396510 の反応式
[CH2:1]([O:8][C:9]1[CH:13]=[C:12](C(OCC)=O)[N:11]([CH2:19][CH2:20][NH:21][C:22]([O:24]C(C)(C)C)=O)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl.O1CCOCC1.O>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]2[C:22](=[O:24])[NH:21][CH2:20][CH2:19][N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 10340Sodium CarbonateHCID 86706489ethyl 3-(benzyloxy)-1-{2-[(tert-butoxycarbonyl)amino]ethyl}-1H-pyrazole-5-carboxylate

生成物 1

HCID 727147872-(benzyloxy)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one収率 99%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒
HCID 31275
1,4-Dioxane
溶媒

実験手順

Ethyl 3-(benzyloxy)-1-{2-[(tert-butoxycarbonyl)amino]ethyl}-1H-pyrazole-5-carboxylate (0.51 g, 1.31 mmol) was dissolved in a 4 M solution of HCl in 1,4-dioxane (6.53 mL). The mixture was stirred at room temperature for 1 hour and then made basic using a saturated solution of Na2CO3. The mixture was stirred at room temperature for 1 hour, diluted with water and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; 7 M solution of ammonia in MeOH in DCM 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-(benzyloxy)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one (0.31 g, 99% yield) as a white solid. C13H13N3O2. 1H NMR (400 MHz, CDCl3) δ ppm 3.63-3.73 (m, 2H), 4.13 (dd, J=6.9, 5.4 Hz, 2H), 5.13 (s, 2H), 6.20 (s, 1H), 7.22 (br. s., 1H), 7.23-7.28 (m, 1H), 7.28-7.34 (m, 2H), 7.34-7.41 (m, 2H).

後処理

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvents evaporated in vacuo
  7. customThe crude product was purified by flash column chromatography (silica; 7 M solution of ammonia in MeOH in DCM 0/100 to 10/90)
  8. customThe desired fractions were collected
  9. customthe solvents evaporated in vacuo

出典と根拠

ORDレコード
ord-43a5880769934af29a68ff4ab455dc9d
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08901125B2

反応ノート

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