HCID 19809507, compound → HCID 19809494, compound

A solution of (±)5-(2-methoxycarbonyl-1,3-oxazol-5-yl)-1-azabicyclo[3.2.1]octane (E9) (0.2g, 0.8 mmole) in dry toluene (12 ml), cooled in ice, under nitrogen, was treated with diisobutylaluminium hydride (1.04 ml of a 1.5M solution in toluene, 1.6 mmole) over 15 min. The reaction was allowed to warm up to room temperature over 1h, then more diisobutylaluminium hydride (1.6 mmole) was added and the reaction left for a further 1h. After quenching with methanol (8 ml) and 10% sodium hydroxide solution (10 ml), potassium carbonate was added until the aqueous layer was saturated. The organic layer was separated and the aqueous phase was extracted with chloroform. The combined organic layers were dried over sodium sulphate 9 then concentrated in vacuo. Purification of the residue on neutral alumina in a gradient of 0-5% methanol in chloroform afforded the title compound (E10) as a gum (0.1g, 55%) which was converted into the hydrochloride salt m.p. 152° C. (dec.) (from methanol-ether).

1. customAfter quenching with methanol (8 ml) and 10% sodium hydroxide solution (10 ml), potassium carbonate
2. additionwas added until the aqueous layer
3. customThe organic layer was separated
4. extractionthe aqueous phase was extracted with chloroform
5. dry with materialThe combined organic layers were dried over sodium sulphate 9
6. concentrationthen concentrated in vacuo
7. customPurification of the residue on neutral alumina in a gradient of 0-5% methanol in chloroform

ORD record

ord-f6e014a3ab994cd9a290bf81a1bdc98d

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05166357