Hydrochloric Acid → (3R,5S)-5-(Methoxycarbonyl)pyrrolidin-3-yl 4-vinyl-1,3-dihydro-2H-isoindole-2-carboxylate Hydrochloride

HRID 2377601ノート

反応式

HRID 2377601 の反応式
[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][N:6]([C:12]([O:14][C@H:15]1[CH2:19][N:18](C(OC(C)(C)C)=O)[C@H:17]([C:27]([O:29][CH3:30])=[O:28])[CH2:16]1)=[O:13])[CH2:7]2)=[CH2:2].[ClH:31]>C(OCC)(=O)C>[ClH:31].[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][N:6]([C:12]([O:14][C@@H:15]1[CH2:16][C@@H:17]([C:27]([O:29][CH3:30])=[O:28])[NH:18][CH2:19]1)=[O:13])[CH2:7]2)=[CH2:2]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 453783721-t-Butyl 2-methyl (2S,4R)-4-{[(4-vinyl-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboxylate

生成物 1

HCID 45379932(3R,5S)-5-(Methoxycarbonyl)pyrrolidin-3-yl 4-vinyl-1,3-dihydro-2H-isoindole-2-carboxylate Hydrochloride収率 95%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 1-tert-Butyl 2-methyl (2S,4R)-4-{[(4-vinyl-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboxylate (13.9 g, 33.4 mmol) in ethyl acetate (700 mL) was cooled in an ice bath the saturated with hydrogen chloride gas. The reaction flask was sealed and allowed to warm to room temperature. After 3.5 h the solvent was removed by evaporation to give the title compound as a gray solid, 11.2 g, 95% yield). 1H NMR (500 MHz, ppm, CD3OD) δ 7.47-7.45 (m, 1 H), 7.32-7.31 (m, 1 H), 7.26-7.21 (m, 1 H), 6.79-6.73 (m, 1 H), 5.79-5.73 (m, 1 H), 5.46 (s, 1 H), 5.41-5.38 (m, 1 H), 4.80-4.72 (m, 4 H), 3.91 (s, 3 H), 3.74-3.63 (m, 2 H), 2.77-2.71 (m, 1 H), 2.51-2.46 (m, 1 H), LRMS (ESI) m/z 317 [(M+H)+; calcd for C17H21N2O4: 317].

後処理

  1. customThe reaction flask was sealed
  2. customAfter 3.5 h the solvent was removed by evaporation

出典と根拠

ORDレコード
ord-698b0bd222404de1a3582664e6085096
出典データセット
uspto-grants-2008_12
特許番号
US07470664B2

反応ノート

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