Tetrahydrofuran → Tert-butyl 4-[4-(4-morpholinylmethyl)anilino]-1-piperidinecarboxylate

HRID 1068040

Reaktionsgleichung

Reaktionsgleichung von HRID 1068040
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.O1CCCC1.O=[C:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[N:7]1([CH2:6][C:5]2[CH:13]=[CH:14][C:2]([NH:1][CH:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]3)=[CH:3][CH:4]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 7768514-(Morpholinomethyl)anilineHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 21192593Tert-butyl 4-[4-(4-morpholinylmethyl)anilino]-1-piperidinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A flask containing 4-(4-aminobenzyl)morpholine from Preparation No. 22 (0.48 g) is treated with tetrahydrofuran (10 mL) and tert-butyl 4-oxo-1-piperidinecarboxylate (0.60 gm) under an argon atmosphere. The solution is treated with acetic acid (0.20 mL) followed by sodium triacetoxyborohydride (0.80 g). After stirring 3 days, the mixture is concentrated under reduced pressure. The residue is partitioned between dichloromethane and dilute aqueous sodium hydroxide. The aqueous is back-extracted with additional portions of dichloromethane. The combined organic layer is washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue is flash column chromatographed on silica gel eluting with 2% to 6% methanol in dichloromethane to afford 0.96 g of tert-butyl 4-[4-(4-morpholinylmethyl)anilino]-1-piperidinecarboxylate as a tan solid.

Aufarbeitung

  1. customfrom Preparation No
  2. concentrationthe mixture is concentrated under reduced pressure
  3. customThe residue is partitioned between dichloromethane and dilute aqueous sodium hydroxide
  4. extractionThe aqueous is back-extracted with additional portions of dichloromethane
  5. washThe combined organic layer is washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customchromatographed on silica gel eluting with 2% to 6% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-a5343a0bf97e4248adc7f61cfc25499a
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248739B1

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