Benzyl carbamate → HCID 25260225、化合物

HRID 2280698

反応式

HRID 2280698 の反応式
[O:1]1[CH2:6][CH:5]=[CH:4][C:3](=[O:7])[CH2:2]1.[C:8](=[O:18])([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH2:9].O.O.O.O.O.[N+]([O-])([O-])=O.[Bi+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>C(Cl)Cl>[O:7]=[C:3]1[CH2:2][O:1][CH2:6][CH:5]([NH:9][C:8](=[O:18])[O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:4]1

参加物

5

反応物 3

HCID 12136Benzyl carbamateHCID 160911Bismuth nitrate pentahydrateHCID 46725963,6-dihydro-2H-pyran-3-one

生成物 1

HCID 25260225HCID 25260225、化合物収率 73.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

2H-pyran-3(6H)-one (2.33 g, 23.75 mmol), benzyl carbamate (4.31 g, 28.5 mmol), and DCM (2.375 mL) were added to a small vial and stirred vigorously. To the thick syrup was added bismuth(III) nitrate pentahydrate (1.728 g, 3.56 mmol). The vial was capped and the reaction was stirred vigorously overnight. The reaction was diluted with DCM and filtered through a pad of celite. The filtrate was condensed and purified on a 100G SNAP Biotage column (10-100% ethyl acetate in hexane) to give benzyl 5-oxotetrahydro-2H-pyran-3-ylcarbamate (4.35 g, 17.45 mmol, 73.5% yield) as a pale yellow oil; 1H NMR (400 MHz, CDCl3) δ ppm 7.28-7.41 (m, 5H), 5.20-5.28 (m, 1H), 5.05-5.15 (m, 2H), 4.24-4.35 (m, 1H), 4.01-4.06 (m, 1H), 3.89-3.95 (m, 1H), 3.80-3.87 (m, 1H), 2.73 (d, J=5.47 Hz, 1H), 2.64-2.71 (m, 1H).

後処理

  1. customThe vial was capped
  2. stirringthe reaction was stirred vigorously overnight
  3. filtrationfiltered through a pad of celite
  4. customcondensed
  5. custompurified on a 100G SNAP Biotage column (10-100% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-45bac57ddec846539113dd5d9e70d1d7
出典データセット
uspto-grants-2015_09
特許番号
US09139534B2

関連ノート

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