Ethanol → (R)-3-[(S)-(2,3-Dichlorophenoxy)(tetrahydropyran-4-yl)-methyl]pyrrolidine

HRID 1254990ノート

反応式

HRID 1254990 の反応式
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([C@@H:13]([OH:20])[CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:9]1)=O)(C)(C)C.[H-].[Na+].[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26](F)[C:25]=1[Cl:31].CCO>CN(C=O)C.Cl>[Cl:23][C:24]1[C:25]([Cl:31])=[CH:26][CH:27]=[CH:28][C:29]=1[O:20][C@@H:13]([CH:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)[C@@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1

参加物

7

反応物 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 119011Benzene, 1,2-dichloro-3-fluoro-HCID 66859077(R)-3-[(S)-Hydroxy(tetrahydropyran-4-yl)methyl]pyrrolidine-1-carboxylic Acid t-Butyl Ester

生成物 1

HCID 58120262(R)-3-[(S)-(2,3-Dichlorophenoxy)(tetrahydropyran-4-yl)-methyl]pyrrolidine

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 6228Dimethylformamide溶媒

実験手順

(R)-3-[(S)-Hydroxy(tetrahydropyran-4-yl)methyl]pyrrolidine-1-carboxylic acid t-butyl ester (30 mg, 0.1 mmol) was dissolved in DMF (380 μL). NaH (3.0 mg, 126 μmol) was added and the mixture was stirred at room temperature for 15 minutes. 1,2-Dichloro-3-fluorobenzene (34.7 mg, 210 μmol) was added and the mixture was stirred at 100° C. overnight. The mixture was concentrated then dissolved in 1.2M HCl in EtOH (510 μL, 610 μmol) and stirred overnight. The product was concentrated and purified by preparative HPLC to yield the title compound as a mono-TFA salt (10.8 mg, purity 100%). MS m/z: [M+H]+ calcd for C16H21Cl2NO2, 330.10. found 330.0.

後処理

  1. stirringthe mixture was stirred at 100° C. overnight
  2. concentrationThe mixture was concentrated
  3. stirringstirred overnight
  4. concentrationThe product was concentrated
  5. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-8f50834ee99548eebcf6acfadc69f461
出典データセット
uspto-grants-2013_06
特許番号
US08455665B2

反応ノート

読み込み中…