Benzyl carbamate → HCID 25260225, 화합물

HRID 2280698

반응식

HRID 2280698 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 25260225HCID 25260225, 화합물수율 73.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-45bac57ddec846539113dd5d9e70d1d7
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139534B2

연결된 노트

불러오는 중…