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Hydrochloric Acid → Tert-butyl 4-[2-(5-methylene-7-oxo-[1,3]dioxolo[4,5-f]isoindol-6-yl)ethyl]piperidine-1-carboxylate

HRID 528509
ノート
印刷プレビュー

反応式

HRID 528509 の反応式
O=[C:2]1[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][O:13][C:7]3=[CH:6][C:5]=2[C:4](=[O:14])[N:3]1[CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1.O1CCC[CH2:31]1.C[Mg]I.C(OCC)C.Cl>O.C(OCC)(=O)C>[CH2:31]=[C:2]1[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][O:13][C:7]3=[CH:6][C:5]=2[C:4](=[O:14])[N:3]1[CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:19][CH2:18]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 90064408Tert-butyl 4-[2-(5,7-dioxo-[1,3]dioxolo[4,5-f]isoindol-6-yl) ethyl]piperidine-1-carboxylateHCID 178467823HCID 178467823、化合物

生成物 1

HCID 90064412Tert-butyl 4-[2-(5-methylene-7-oxo-[1,3]dioxolo[4,5-f]isoindol-6-yl)ethyl]piperidine-1-carboxylate収率 63.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
5 °C

実験手順

To a reaction vessel, 75 g (0.19 mol) compound XI and 500 ml tetrahydrofuran were added while stirring under nitrogen, The mixture was cooled to 0-10° C., 400 ml 1.2N methylmagnesium iodide/ethyl ether solution was slowly added into the reaction vessel, the reaction was kept for 1 h, a minor amount of water was added until there was no bubble formed, concentrated hydrochloric acid was added to adjust the pH to acidic, the reaction was kept for 15 min, 500 ml ethyl acetate and 300 ml water were added, extracted, washed, the organic layer was collected, dried over sodium sulfate, filtered, the filtrate was concentrated to a minor amount, petroleum ether was added, solid was precipitated out, filtered, dried, and 47.6 g compound IX-1 was obtained, with yield of 63.8%. H NMR (DMSO-d6): δ 0.95-1.05 (m, 2H), 1.38 (s, 10H), 1.48 (q, 2H, J=7.0 Hz), 1.71 (d, 2H, J=12.2 Hz), 2.65 (br s, 2H), 3.70 (t, 2H, J=7.2 Hz), 3.90 (d, 2H, J=11.6 Hz), 4.95 (s, 1H), 5.34 (s, 1H), 6.17 (s, 2H), 7.15 (s, 1H), 7.53 (s, 1H); MS (ESI): m/z 423 [M+Na]+.

後処理

  1. customformed
  2. waitwas kept for 15 min
  3. extractionextracted
  4. washwashed
  5. customthe organic layer was collected
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated to a minor amount, petroleum ether
  9. additionwas added
  10. customsolid was precipitated out
  11. filtrationfiltered
  12. customdried

出典と根拠

ORDレコード
ord-8f3328c0b6c342e5a95c648d44323f52
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09346818B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート