Reaktion #714102

ord-a1b967c2e1f840639ba3ab3050becc96

Reaktionsgleichung

Cc1cc(-c2ccc(C(F)(F)F)cc2)nc([C@H]2CC[C@]3(CCNC3=O)N2C(=O)OC(C)(C)C)n1
tert-butyl (2R,5R)-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate
Cc1cc(-c2ccc(C(F)(F)F)cc2)nc([C@H]2CC[C@]3(CCNC3=O)N2)n1
(2R,5R)-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]-nonan-6-one
Cl
HCl
ClC(Cl)Cl
CHCl3
→
Cc1cc(-c2ccc(C(F)(F)F)cc2)nc([C@H]2CC[C@]3(CCNC3=O)N2)n1.Cl
(2R,5R)-2-[4-methyl-6-[4-(trifluoromethyl)-phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride

Edukte

Cc1cc(-c2ccc(C(F)(F)F)cc2)nc([C@H]2CC[C@]3(CCNC3=O)N2C(=O)OC(C)(C)C)n1
tert-butyl (2R,5R)-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate
Cc1cc(-c2ccc(C(F)(F)F)cc2)nc([C@H]2CC[C@]3(CCNC3=O)N2)n1
(2R,5R)-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]-nonan-6-one
Cl
HCl
ClC(Cl)Cl
CHCl3

Reagenzien

Keine

Lösungsmittel

CCOCC
ether

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

In a similar manner, tert-butyl (2R,5R)-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate (37 mg) was converted first to the free base (2R,5R)-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]-nonan-6-one (27 mg); m/z 377 (M+H+); Optical Rotation α[D/20)]=+32.1 (c=0.56, CHCl3). This material was subsequently treated with HCl in ether to form (2R,5R)-2-[4-methyl-6-[4-(trifluoromethyl)-phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride (E42) (32 mg); m/z 377 (M+H+).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09309254B2uspto-grants-2016_04