Water → {(S)-6-[(R)-4-(8-Aza-bicyclo[3.2.1]oct-8-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 1422631ノート

反応式

HRID 1422631 の反応式
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2.C([O-])([O-])=O.[K+].[K+].[CH3:15][O:16][C:17](=[O:44])[CH2:18][C@H:19]1[C:23]2[CH:24]=[CH:25][C:26]([O:28][C@H:29]3[C:37]4[C:32](=[C:33]([CH2:42]Br)[C:34]([C:38]([F:41])([F:40])[F:39])=[CH:35][CH:36]=4)[CH2:31][CH2:30]3)=[CH:27][C:22]=2[O:21][CH2:20]1.O>CN(C)C=O.[Cl-].[Na+].O>[CH3:15][O:16][C:17](=[O:44])[CH2:18][C@H:19]1[C:23]2[CH:24]=[CH:25][C:26]([O:28][C@H:29]3[C:37]4[C:32](=[C:33]([CH2:42][N:8]5[CH:5]6[CH2:6][CH2:7][CH:1]5[CH2:2][CH2:3][CH2:4]6)[C:34]([C:38]([F:41])([F:39])[F:40])=[CH:35][CH:36]=4)[CH2:31][CH2:30]3)=[CH:27][C:22]=2[O:21][CH2:20]1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1360978-Azabicyclo(3.2.1)octaneHCID 86700813{(S)-6-[(R)-4-Bromomethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

生成物 1

HCID 90313855{(S)-6-[(R)-4-(8-Aza-bicyclo[3.2.1]oct-8-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

8-Aza-bicyclo[3.2.1]octane (19 mg), KI (27 mg), and K2CO3 (45 mg) are added to a solution of {(S)-6-[(R)-4-bromomethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (80 mg) in N,N-dimethylformamide (2 mL) at room temperature. The resulting mixture is stirred at room temperature overnight. Water and brine are added and the mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated to give the crude title compound that is submitted to the next reaction step without further purification. LC (method 6): tR=0.93 min; Mass spectrum (ESI+): m/z=516 [M+H]+.

後処理

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialThe combined extracts are dried (Na2SO4)
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-57504d3f0aad4ebdbea8c1b9101c4fc5
出典データセット
uspto-grants-2015_01
特許番号
US08927531B2

反応ノート

読み込み中…