Potassium tert-butoxide → (7S,8aS)-tert-butyl 7-(5-cyclopropylpyrazin-2-yloxy)hexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate

HRID 240436ノート

反応式

HRID 240436 の反応式
[OH:1][C@@H:2]1[CH2:17][N:5]2[CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C@@H:4]2[CH2:3]1.CC(C)([O-])C.[K+].Br[C:25]1[CH:30]=[N:29][C:28]([CH:31]2[CH2:33][CH2:32]2)=[CH:27][N:26]=1>O1CCCC1>[CH:31]1([C:28]2[N:29]=[CH:30][C:25]([O:1][C@@H:2]3[CH2:17][N:5]4[CH2:6][CH2:7][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:9][C@@H:4]4[CH2:3]3)=[N:26][CH:27]=2)[CH2:33][CH2:32]1

参加物

5

反応物 3

HCID 23665647Potassium tert-butoxideHCID 457876352-Bromo-5-cyclopropylpyrazineHCID 72698247(7S,8aS)-tert-butyl 7-hydroxyhexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate

生成物 1

HCID 86680448(7S,8aS)-tert-butyl 7-(5-cyclopropylpyrazin-2-yloxy)hexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of (7S,8aS)-tert-butyl 7-hydroxyhexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (Wuxi Pharma, 0.485 g, 2 mmol) in tetrahydrofuran (0.3 mL) was added potassium tert-butoxide (2.8 mL, 1 M in tetrahydrofuran, 2.8 mmol) followed by a solution of 2-bromo-5-cyclopropylpyrazine (446 mg, 2.24 mmol) in tetrahydrofuran (1 mL). The mixture was stirred at room temperature for 16 hours. The mixture was concentrated, and the residue was purified by chromatography on silica gel (ethyl acetate) to give the titled compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.80 (m, 2H), 0.92 (m, 2H), 1.39 (s, 9H), 1.90 (m, 2H), 2.09 (m, 1H), 2.40 (m, 3H), 2.90 (m, 2H), 3.08 (m, 1H), 3.28 (m, 1H), 3.86-4.08 (m, 2H), 5.27 (m, 1H), 8.11 (m, 2H); MS (ESI) m/z 361 (M+H)+.

後処理

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by chromatography on silica gel (ethyl acetate)

出典と根拠

ORDレコード
ord-16b8b299b1784d15a9c457e7d3af0a19
出典データセット
uspto-grants-2014_02
特許番号
US08648074B2

反応ノート

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