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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 411133Generated: October 26, 2026

(S)-4-(Oxiran-2-ylmethoxy)benzonitrile → tert-Butyl 7-[(2S)-3-(4-cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

https://huagongshe.com/reaction/411133

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(S)-4-(Oxiran-2-ylmethoxy)benzonitrileHCID 6934187—
Reactant3-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonaneHCID 18540412—
SolventPropan-2-ol--water (1/1)HCID 21889133—
Producttert-Butyl 7-[(2S)-3-(4-cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylateHCID 21076121100%

Reaction Steps

A mixture of tert-butyl 9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (prepared in an analogous fashion to the compound of Preparation A(vi) above; 0.72 g, 3.2 mmol) and 4-[(2S)-oxiranylmethoxy]benzonitrile (from step (i) above; 0.56 g, 3.2 mmol) in IPA/water (11 mL of 10:1) was stirred at 60° C. for 18 h. The solvent was then evaporated to give 1.3 g (100%) of the sub-title compound, which was used in the next step without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06559143B1
Source datasetuspto-grants-2003_05
ORD IDord-0103edb9e12c426190c98ee00d0095ef
Source noteuspto-grants-2003_05