反応式
[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18](O)=[O:19])[CH2:14][CH2:13]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:27][N:28](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:29].[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.CNC.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]1([CH:7]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]([N:28]([CH3:29])[CH3:27])=[O:19])[CH2:14][CH2:13]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1参加物
反応物 5
生成物 1
試薬・触媒・溶媒 1
実験手順
1-[1-(Diphenylmethyl)azetidin-3-yl]piperidine-4-carboxylic acid (0.35 g, 0.9 mmol) was dissolved in DMF (8 mL) and to the solution were added TBTU (0.39 g, 1.2 mmol), DIPEA (0.21 mL, 1.2 mmol) and a solution of dimethylamine (3.0 mL, 2M in THF, 6 mmol). The mixture was stirred at RT for 14 h. An aqueous solution of NaHCO3 was added and the mixture was extracted three times with methylene chloride. The combined organic layers were washed with brine and dried over MgSO4. The solvent was removed by evaporation and the product was purified by reversed phase chromatography (C8) using acetonitrile and aqueous ammonium acetate solution (0.1 M) as eluent. There was obtained 0.20 g (59%) of 1-[1-(diphenylmethyl)azetidin-3-yl]-N,N-dimethylpiperidine-4-carboxamide. 1H NMR (500 MHz, CDCl3): δ 1.6-2.0 (cm, 6H), 2.4-2.5 (m, 1H), 2.8 (m, 2H), 2.9-3.0 (m, 5H), 3.1 (s, 3H), 3.4 (t, 2H), 4.4 (s, 1H), 7.2 (t, 2H), 7.3 (t, 4H), 7.4 (d, 4H); LCMS: m/z 378 (M+1)+.
後処理
- extractionthe mixture was extracted three times with methylene chloride
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- customThe solvent was removed by evaporation
- customthe product was purified by reversed phase chromatography (C8)
出典と根拠
- ORDレコード
- ord-f39b68eac6394999876f91dca8a54946
- 出典データセット
- uspto-grants-2012_01
- 特許番号
- US08106208B2
関連ノート
読み込み中…