反応式
C(O)(=O)C.[F:5][C:6]([F:26])([F:25])[C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[C:10]([NH:12][CH2:13][C:14]([NH:16][C@@H:17]1[CH2:21][CH2:20][NH:19][CH2:18]1)=[O:15])=[O:11].[CH2:27]([C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1)[CH2:28][CH2:29][CH3:30].[BH3-]C#N.[Na+]>CO>[CH2:27]([C:31]1[CH:32]=[CH:33][C:34]([CH2:35][N:19]2[CH2:20][CH2:21][C@@H:17]([NH:16][C:14](=[O:15])[CH2:13][NH:12][C:10](=[O:11])[C:9]3[CH:22]=[CH:23][CH:24]=[C:7]([C:6]([F:5])([F:25])[F:26])[CH:8]=3)[CH2:18]2)=[CH:37][CH:38]=1)[CH2:28][CH2:29][CH3:30]参加物
6
反応条件
- 温度
- 60 °C
実験手順
Acetic acid (0.060 mL) was added to a mixture of (R)-3-[N-[3-(trifluoromethyl)benzoyl]glycyl]aminopyrrolidine (0.050 mL) with 4-butylbenzaldehyde (0.18 mmol), NaBH3CN (0.23 mmol) and methanol (1.85 mL). The resulting reaction mixture was stirred at 60° C. for 12 hours, cooled to room temperature, loaded onto a Varian™ SCX column and washed with methanol (15 mL). The obtained crude product was eluted with a solution of 2 M NH3 in methanol (5 mL) and concentrated to thereby afford (R)-1-(4-butylbenzyl)-3-[[N-(3-trifluoromethylbenzoyl)glycyl]amino]pyrrolidine (Compd. No. 1648) (20.6 mg, 89%). The purity was determined by RPLC/MS (91%). ESI/MS m/e 462.2 (M++H, C25H30F3N3O2).
後処理
- customThe resulting reaction mixture
- temperaturecooled to room temperature
- washwashed with methanol (15 mL)
- customThe obtained crude product
- washwas eluted with a solution of 2 M NH3 in methanol (5 mL)
- concentrationconcentrated to thereby afford (R)-1-(4-butylbenzyl)-3-[[N-(3-trifluoromethylbenzoyl)glycyl]amino]pyrrolidine (Compd. No
出典と根拠
- ORDレコード
- ord-47304ef1add247eb94257c007d3114db
- 出典データセット
- uspto-grants-2008_06
- 特許番号
- US07390830B1
関連ノート
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