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Methanol → tert-butyl 4-[2-(5-hydroxy-7-oxo-5H-[1,3]dioxolo[4,5-f]isoindol-6-yl)ethyl]piperidine-1-carboxylate

HRID 528503
ノート
印刷プレビュー

反応式

HRID 528503 の反応式
[O:1]=[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.CO.O1CCCC1.[BH4-].[Na+]>O>[OH:14][CH:4]1[C:5]2[CH:6]=[C:7]3[O:13][CH2:12][O:11][C:8]3=[CH:9][C:10]=2[C:2](=[O:1])[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 90064408Tert-butyl 4-[2-(5,7-dioxo-[1,3]dioxolo[4,5-f]isoindol-6-yl) ethyl]piperidine-1-carboxylate

生成物 1

HCID 90064479tert-butyl 4-[2-(5-hydroxy-7-oxo-5H-[1,3]dioxolo[4,5-f]isoindol-6-yl)ethyl]piperidine-1-carboxylate収率 70%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a reaction vessel, 92 g (0.23 mol) compound XI, 250 ml methanol and 250 ml tetrahydrofuran were added while stirring, the mixture was cooled to 0˜10° C., 10 g (0.26 mol) sodium borohydride was added, the reaction was kept at 0˜10° C. for 20-30 min, 100 ml water was added, the reaction mixture was concentrated to dry under reduced pressure (at 45° C.), The residue was added 500 ml ethyl acetate and 300 ml water, and extracted, the organic layer was collected, dried over sodium sulfate, concentrated to a minor amount, 300 ml petroleum ether was added, a solid was precipitated out, filtered, the filter cake was washed wth petroleum ether, dried, and 64.7 g compound VII-1 was obtained, with yield of 70%. 1H NMR (DMSO-d6): δ 0.95-1.04 (m, 2H), 1.39 (s, 10H), 1.51 (m, 2H), 1.70 (dd, 2H, J=25.0, 12.4 Hz), 2.65 (br s, 2H), 3.23-3.30 (m, 1H), 3.54-3.61 (m, 1H), 3.90 (d, 2H, J=10.0 Hz), 5.67 (d, 1H, J=8.9 Hz), 6.12 (s, 1H), 6.13 (s, 1H), 6.50 (d, 1H, J=9.0 Hz), 7.08 (s, 1H), 7.09 (s, 1H); MS (ESI): m/z 427 [M+Na]+.

後処理

  1. temperaturethe mixture was cooled to 0˜10° C.
  2. concentrationthe reaction mixture was concentrated
  3. customto dry under reduced pressure (at 45° C.)
  4. additionThe residue was added 500 ml ethyl acetate and 300 ml water
  5. extractionextracted
  6. customthe organic layer was collected
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to a minor amount, 300 ml petroleum ether
  9. additionwas added
  10. customa solid was precipitated out
  11. filtrationfiltered
  12. washthe filter cake was washed wth petroleum ether
  13. customdried

出典と根拠

ORDレコード
ord-4f4f03fd14db462c868fbd12c798df63
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

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