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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 265907Generated: October 31, 2026

Diethyl Ether → Tert-butyl 3-(1-hydroxyethyl)azetidine-1-carboxylate

https://huagongshe.com/reaction/265907

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantLithium borohydrideHCID 4148881—
ReactantTert-butyl 3-(2-ethoxy-2-oxoethyl)azetidine-1-carboxylateHCID 15256325—
ProductTert-butyl 3-(1-hydroxyethyl)azetidine-1-carboxylateHCID 58348207—

Reaction Conditions

Temperature55 °C

Reaction Steps

A stirred solution of 33-4 (0.96 g, 3.9 mmol) in ether (20 mL) at ambient temperature was treated with LiBH4 (0.34 g, 15.8 mmol) then heated to 55° C. After 45 min the cooled reaction was quenched with 5% KHSO4 (10 mL) and then diluted with EtOAc. The organic phase was washed with 5% KHSO4 and brine, dried (MgSO4), and concentrated to give 33-5 (0.79 g) as a colorless oil. Rf 0.46 (silica, EtOAc).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05648368
Source datasetuspto-grants-1997_07
ORD IDord-4ef28c0fd91c4258a636a83308720e66
Source noteuspto-grants-1997_07