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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 499080Generated: October 28, 2026

Water → HCID 59420847, compound

https://huagongshe.com/reaction/499080

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 numberUS07767672B2
Source datasetuspto-grants-2010_08
ORD IDord-c2497b44c4634b8b89e0439faee8de78
Source noteuspto-grants-2010_08