Norcamphor → 1'-(bicyclo[2.2.1]heptan-2-yl)-N-(pentan-3-yl)spiro[indene-1,4'-piperidine]-3-carboxamide

A mixture of (F2) (0.020 g, 0.05 mmol), titanium (IV) isopropoxide (0.045 mL, 0.15 mmol) and (1R,4S)-bicyclo[2.2.1]heptan-2-one (3 eq) was stirred at room temperature for 18 h in dichloroethane (0.5 mL). Sodium triacetoxyborohydride (0.011 g, 0.050 mmol) was added and the mixture stirred at room temperature for 1 h. The solvent was evaporated and 6N NaOH (0.5 mL) and methanol (1 mL) was added and then triturated to give a white solid that was washed with methanol (1 mL) and EtOAc (1 mL). The filtrate was concentrated under reduced pressure to afford the crude product which was purified by reverse phase preparative HPLC to afford 1′-(bicyclo[2.2.1]heptan-2-yl)-N-(pentan-3-yl)spiro[indene-1,4′-piperidine]-3-carboxamide (Compound No. 14) (0.013 g). LC/MS (10-90% over 3 min with 0.9% FA) m/z 324.1 (M+1), retention time 2.2 minutes.

1. customThe solvent was evaporated
2. addition6N NaOH (0.5 mL) and methanol (1 mL) was added
3. customtriturated
4. customto give a white solid
5. washthat was washed with methanol (1 mL) and EtOAc (1 mL)
6. concentrationThe filtrate was concentrated under reduced pressure
7. customto afford the crude product which
8. customwas purified by reverse phase preparative HPLC

ORD-Eintrag

ord-c49b317282534b7ea482afc586683ca0

Quelldatensatz

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07858790B2