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Sodium borohydride → Tert-butyl 4-(hydroxy(pyridin-3-yl)methyl)piperidine-1-carboxylate

HRID 862725
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 862725
[CH3:1][C:2]([CH3:21])([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:14])[CH2:9][CH2:8]1)=[O:6])[CH3:3].[BH4-].[Na+]>CO>[CH3:3][C:2]([CH3:21])([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[OH:14])[CH2:9][CH2:8]1)=[O:6])[CH3:1]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 19698705tert-Butyl 4-nicotinoylpiperidine-1-carboxylate

Produkt 1

HCID 18538796Tert-butyl 4-(hydroxy(pyridin-3-yl)methyl)piperidine-1-carboxylateAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1-(1,1-dimethylethyloxycarbonyl)-4-(3-pyridinoyl)piperidine (5.0 g, 17.22 mmol) in methanol (75 mL) was cooled to 0° C. and sodium borohydride (1.30 g, 34.44 mmol) was added in four portions. The mixture was stirred at 0° C. for 1 h. The solvent was evaporated and the residue was partitioned between water (25 mL) and ethyl acetate (100 mL, 2×50 mL). The organic extracts were washed sequentially with 1N aqueous sodium hydroxide (25 mL) and brine (25 mL), combined, dried over Na2SO4, filtered and evaporated to afford the title alcohol as a white foam (5.02 g, 17.17 mmol, 99%). 1H NMR: δ8.45 (brs, 2H, H--C(2'), H--C(6')), 7.85 (brd, J=8.4 Hz, 1H, H--C(4')), 7.28 (dd, J=4.9, 8.4 Hz, 1H, H--C(5')), 4.43 (d, J=7.1 Hz, 1H, CHOH), 4.08 (m, 2H, eq-H--C(2)), 3.28 (exs, 1H, CHOH), 2.62 (m, 2H, ax-H--C(2)), 1.90 (m, 2H, eq-H--C(3)), 1.77 (m, 1H, H--C(4)), 1.43 (s, 9H, (CH3)3C), 1.28 (m, 2H, ax-H--C(3)). CIMS: m/z 293 (87%, (M+H)+ for C16H24N2O3), 265 (19), 237 (100), 219 (14), 175 (24).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between water (25 mL) and ethyl acetate (100 mL, 2×50 mL)
  3. washThe organic extracts were washed sequentially with 1N aqueous sodium hydroxide (25 mL) and brine (25 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ddd5775e01524d35b5299cfa71068893
Quelldatensatz
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05719166

Notizen zur Reaktion

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