Reaktion #425182

ord-ec99373a8018471e9750ebb64e3747d5

Reaktionsgleichung

Cn1cccn1
1-methylpyrazole
[Li][CH2]CCC
n-butyl lithium
CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H]2O[C@H]2C1
tert-butyl(dimethyl) [(1S*,3R*,6R*)-7-oxabicyclo[4.1.0]hept-3-yloxy]silane
→
Cn1nccc1[C@H]1CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O
title compound
Ausbeute 52.0%
Cn1nccc1[C@H]1CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O
(1S*,2R*,5R*)-5-{[Tert-butyl(dimethyl)silyl]oxy}-2-(1-methyl-1H-pyrazol-5-yl)cyclohexanol
Ausbeute 52.0%

Edukte

Cn1cccn1
1-methylpyrazole
[Li][CH2]CCC
n-butyl lithium
CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H]2O[C@H]2C1
tert-butyl(dimethyl) [(1S*,3R*,6R*)-7-oxabicyclo[4.1.0]hept-3-yloxy]silane

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction and aftertreatment

Vorschrift

The reaction and aftertreatment were conducted in the same manner as in Example 4a by using the 1-methylpyrazole (500 mg, 6.09 mmol), n-butyl lithium (2.69 M solution in hexane, 2.37 mL, 6.37 mmol), tert-butyl(dimethyl) [(1S*,3R*,6R*)-7-oxabicyclo[4.1.0]hept-3-yloxy]silane (J. Pharm. Pharmacol., 49, 835-842, 1997; 1.32 g, 5.78 mmol) and THF (30 mL), to yield the title compound (932 mg, 52%) as a colorless solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08889741B2uspto-grants-2014_11