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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
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 528503
[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
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Komponenten

6

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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]+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4f4f03fd14db462c868fbd12c798df63
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09346818B2

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