Methanol → 4-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzyl alcohol

HRID 506866

Reaktionsgleichung

Reaktionsgleichung von HRID 506866
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.C1COCC1.CO>C1COCC1>[OH:19][CH2:18][C:17]1[CH:16]=[CH:15][C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH2:12]2)=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuran2×HCID 27955084-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acid

Produkt 1

HCID 27955104-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzyl alcohol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(4-(tert-Butoxycarbonyl)piperazin-1-yl)benzoic acid (10 g, 32.64 mmol) was dissolved in anhydrous THF (200 mL) under nitrogen at 0° C. and BH3.THF (1M in THF, 65.3 mL, 65.3 mmol) was added over 15 min. The reaction was maintained at this temperature and after 3 h a further portion of BH3.THF (1M in THF, 10 mL, 10 mmol) was added. After 2 h, MeOH (30 mL) was added and the reaction was warmed to rt. The reaction mixture was partitioned between EtOAc (150 mL) and brine (200 mL). The aqueous layer was re-extracted with EtOAc (100 mL) and the combined organics were washed with a saturated aqueous solution of NaHCO3 (150 mL) and then dried (MgSO4) and filtered. On concentration of the solution the title compound (8.57 g, 90%) precipitated as a white solid and was collected by filtration. 1H NMR (CDCl3) 1.51 (9H, s), 8.14 (4H, t), 3.62 (4H, t), 4.62 (2H, d), 6.94 (2H, d), 7.31 (2H, d).

Aufarbeitung

  1. additionwas added
  2. customThe reaction mixture was partitioned between EtOAc (150 mL) and brine (200 mL)
  3. extractionThe aqueous layer was re-extracted with EtOAc (100 mL)
  4. washthe combined organics were washed with a saturated aqueous solution of NaHCO3 (150 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customOn concentration of the solution the title compound (8.57 g, 90%) precipitated as a white solid
  8. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-66e52f37155145bbb3bb4261ef439080
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786120B2

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