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Lithium borohydride → 1-(3-Hydroxy-propyl)-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester

HRID 500961
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 500961
[Li+].[BH4-].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2[N:16]([CH2:29][CH2:30][C:31](OC)=[O:32])[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2[N:16]([CH2:29][CH2:30][CH2:31][OH:32])[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:21][CH:20]=3)[C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]
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Komponenten

4

Edukt 2

HCID 4148881Lithium borohydride2×HCID 684627001-(2-Methoxycarbonyl-ethyl)-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester

Produkt 1

HCID 684611921-(3-Hydroxy-propyl)-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl esterAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

A solution of LiBH4 (26 mg, 1.2 mmol) in THF (0.5 mL) was added to a 0° C. solution of 1-(2-methoxycarbonyl-ethyl)-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester (317 mg, 0.70 mmol) in THF (4.0 mL). The mixture was stirred for 5 min then additional LiBH4 (15 mg) was added and stirring continued for 17 h. The mixture was partitioned between EtOAc (80 mL) and saturated aqueous NaHCO3 (20 mL). The aqueous layer was extracted with EtOAc (2×20 mL). The combined extracts were dried over Na2SO4 and concentrated. Column chromatography (silica, 0-8% MeOH/CH2Cl2) afforded 268 mg (95%) of the title compound. HPLC (reverse phase conditions), tR=6.82 min. MS (electrospray): m/z calculated for C21H26F3N3O3 [M++Na] 448.18. found 448.10. 1H NMR (CDCl3, 400 MHz): 7.73 (br d, J=8.2 Hz, 2H), 7.65 (br s, 2H), 4.64 (br s, 2H), 4.21 (t, J=6.4 Hz, 2H), 3.76 (br s, 2H), 3.66 (t, J=5.7 Hz, 2H), 2.73 (br t, J=5.4 Hz, 2H), 2.04 (q, J=6.1, 2H), 1.48 (s, 9H).

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 17 h
  3. customThe mixture was partitioned between EtOAc (80 mL) and saturated aqueous NaHCO3 (20 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (2×20 mL)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9ab5a68eab9349dda6fce5ad57db1b4a
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07772236B2

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