Cyclohexene, 1-((trimethylsilyl)oxy)- → Benzyl 3-hydroxy-3-(2-oxocyclohexyl)azetidine-1-carboxylate

HRID 605736

반응식

HRID 605736 반응식
C[Si](C)(C)[O:3][C:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=1.[O:12]=[C:13]1[CH2:16][N:15]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:14]1>O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl>[OH:12][C:13]1([CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]2=[O:3])[CH2:14][N:15]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:16]1

참가 물질

5

반응물 2

HCID 81161Cyclohexene, 1-((trimethylsilyl)oxy)-HCID 10632047Benzyl 3-oxoazetidine-1-carboxylate

생성물 1

HCID 67051703Benzyl 3-hydroxy-3-(2-oxocyclohexyl)azetidine-1-carboxylate수율 92.4%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

A solution of 1-(trimethylsiloxy)cyclohexene (200 mg, 1.17 mmol) and benzyl 3-oxoazetidine-1-carboxylate (289 mg, 1.41 mmol), prepared using procedures similar to those described in Reference 3, in tetrahydrofuran (3.90 mL) was cooled to −78° C. for 10 minutes followed by the addition of titanium tetrachloride (0.13 mL, 1.17 mmol). The reaction mixture stirred for an additional 5 hours at −78° C. The mixture was quenched with aqueous sodium bicarbonate and the aqueous layer was extracted with ether (2×). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was purified on silica gel chromatography column (3:2 hexanes/ethyl acetate) to afford benzyl 3-hydroxy-3-(2-oxocyclohexyl)azetidine-1-carboxylate (328 mg, 37%). 1H NMR (CDCl3): 7.28-7.34 (m, 5H), 5.08 (s, 2H), 4.02 (d, 1H), 3.89 (d, 1H), 3.87 (s, 1H), 3.55 (s, 1H), 2.71 (q, 1H), 2.29-2.43 (m, 2H), 2.11 (s, 2H), 1.95 (s, 1H), 1.66 (d, 3H); MS (EI) for C17H21NO4: 303 (MH+).

후처리

  1. customThe mixture was quenched with aqueous sodium bicarbonate
  2. extractionthe aqueous layer was extracted with ether (2×)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified on silica gel chromatography column (3:2 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-24b2100b35b04700a4d267dd31b14376
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915250B2

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