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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 474008Generated: October 31, 2026

Water → HCID 59420847, compound

https://huagongshe.com/reaction/474008

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactant4-Toluenesulfonyl chlorideHCID 7397—
ReactantPotassium tert-butoxideHCID 23665647—
Reactant1,1-Dimethylethyl 3-hydroxy-3-(2-hydroxy-1,1-dimethylethyl)-1-azetidinecarboxylateHCID 59420711—
SolventTetrahydrofuranHCID 8028—
ProductHCID 59420847HCID 5942084770%

Reaction Steps

To a solution of tert-butyl 3-hydroxy-3-(1-hydroxy-2-methylpropan-2-yl)azetidine-1-carboxylate (0.20 g, 0.82 mmol) in THF (4 ml) was added in rapid succession, KOtBu (0.19 g, 1.72 mmol) and p-toluenesulfonylchloride (0.16 g, 0.82 mmol) and the solution stirred at room temperature for 90 mins. Water (10 ml) was added and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and concentrated to give an oil. The oil was purified by flash column chromatography eluting with 30 to 70% ethylacetate/hexanes to give the title compound as a colorless oil 0.13 g, 70%. 1H NMR (CDCl3, 400 Mhz) 1.25 (6H, s), 1.45 (9H, s), 3.89 (2H, d), 4.12 (2H, d), 4.20 (2H, s).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08637511B2
Source datasetuspto-grants-2014_01
ORD IDord-90f044caf8874f22b9ab387027aa7468
Source noteuspto-grants-2014_01