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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1689270Generated: October 30, 2026

Potassium tert-butoxide → 2-Benzhydryl-5-oxa-2,8-diazaspiro[3.5]nonan-7-one

https://huagongshe.com/reaction/1689270

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium tert-butoxideHCID 23665647—
ReactantN-((1-Benzhydryl-3-hydroxyazetidin-3-yl)methyl)-2-chloroacetamideHCID 57988954—
SolventTetrahydrofuranHCID 8028—
Product2-Benzhydryl-5-oxa-2,8-diazaspiro[3.5]nonan-7-oneHCID 57989264—

Reaction Conditions

Temperature75 °C

Reaction Steps

N-((1-Benzhydryl-3-hydroxyazetidin-3-yl)methyl)-2-chloroacetamide (example 33, step d) (2.6 g) in THF (50 mL) was added dropwise over 90 minutes to a vigorously stirred solution at 75° C. of potassium tert-butoxide (1M in tert-butanol, 15.08 mL) and THF (150 mL) under nitrogen. After the addition was complete the mixture was stirred at 75° C. for 10 minutes and then cooled to room temperature. The solvents were removed under reduced pressure and the residue was partitioned between ethyl acetate and brine. The organic layer was dried over sodium sulphate, filtered and the solvent removed under reduced pressure to afford the subtitled compound. Yield 2.05 g.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08148373B2
Source datasetuspto-grants-2012_04
ORD IDord-e8097f171b4047b8a992836f510946e3
Source noteuspto-grants-2012_04