反応式
[O:1]=[C:2]1[O:7][C@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@H:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:4]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:3]1.C1OCCOCCOCCOCCOC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].I[CH:53]1[CH2:58][CH2:57][N:56]([C:59]([O:61][CH2:62][CH2:63][Si:64]([CH3:67])([CH3:66])[CH3:65])=[O:60])[CH2:55][CH2:54]1.[Cl-].[NH4+]>C1COCC1>[O:1]=[C:2]1[O:7][C@@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:5]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:4]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@@H:3]1[CH:53]1[CH2:54][CH2:55][N:56]([C:59]([O:61][CH2:62][CH2:63][Si:64]([CH3:67])([CH3:66])[CH3:65])=[O:60])[CH2:57][CH2:58]1参加物
7
反応物 5
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- -78 °C
実験手順
4 g of tert-butyl (5S,6R)-2-oxo-5,6-diphenylmorpholine-4-carboxylate were dissolved in 50 ml of THF. 9 ml of 15-crown-5 were added, and the mixture was cooled to −78° C. Then 6.8 ml of a 2 M solution of NaHMDS in THF were added dropwise. The mixture was stirred for 10 min and then 8 g of 2-trimethylsilanylethyl 4-iodopiperidine-1-carboxylate were added dropwise. The mixture was allowed to warm to 0° C. over the course of 6 h, and then the reaction was stopped by adding 200 ml of saturated ammonium chloride solution. The aqueous phase was extracted 3 times with 150 ml of ethyl acetate each time, and the combined organic phases were dried with MgSO4. The solvents were removed in vacuo, and the residue was chromatographed on silica gel.
後処理
- temperatureto warm to 0° C. over the course of 6 h
- extractionThe aqueous phase was extracted 3 times with 150 ml of ethyl acetate each time
- dry with materialthe combined organic phases were dried with MgSO4
- customThe solvents were removed in vacuo
- customthe residue was chromatographed on silica gel
出典と根拠
- ORDレコード
- ord-3e41b89821224680bb8e0715a9e0af01
- 出典データセット
- uspto-grants-2006_03
- 特許番号
- US07008957B2
関連ノート
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