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

HRID 605736

反応式

HRID 605736 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-24b2100b35b04700a4d267dd31b14376
出典データセット
uspto-grants-2011_03
特許番号
US07915250B2

関連ノート

読み込み中…