Potassium Carbonate → tert-Butyl 2-(3-(2-hydroxyethyl)phenethyl)-5-oxa-2,8-diazaspiro[3.5]nonane-8-carboxylate

HRID 1255360Notes

Reaction equation

[CH2:1]1[C:4]2([CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7][CH2:6][O:5]2)[CH2:3][NH:2]1.Br[CH2:18][CH2:19][C:20]1[CH:21]=[C:22]([CH2:26][CH2:27][OH:28])[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[OH:28][CH2:27][CH2:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[CH2:19][CH2:18][N:2]1[CH2:3][C:4]2([CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7][CH2:6][O:5]2)[CH2:1]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of tert-butyl 5-oxa-2,8-diazaspiro[3.5]nonane-8-carboxylate (0.49 g) (example 176 step c), 2-(3-(2-bromoethyl)phenyl)ethanol (0.738 g) [Organometallics 2002, 21(20), 4217] and potassium carbonate (1.187 g) in acetonitrile (30 mL) and water (0.5 mL) was heated at 60° C. for 24 hours. The mixture was cooled to RT and filtered. The solvent was passed through a 10 g SCX cartridge and further acetonitrile then eluted through. The cartridge was then eluted with a 10% solution of 880 ammonia in acetonitrile (80 mL) to bring off product. The solvents were evaporated under reduced pressure and the residue was diluted with acetonitrile and then evaporated to dryness to afford the subtitled compound. Yield 0.610 g.

Workup

temperatureThe mixture was cooled to RT
filtrationfiltered
washthen eluted through
washThe cartridge was then eluted with a 10% solution of 880 ammonia in acetonitrile (80 mL)
customThe solvents were evaporated under reduced pressure
additionthe residue was diluted with acetonitrile
customevaporated to dryness

Sources & evidence

ORD record: ord-9be3fa807bdf4a2397279dbeda03d838
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455483B2

Reaction notes

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