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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1796986Generated: November 2, 2026

Acetic Acid → HCID 69546069, compound

https://huagongshe.com/reaction/1796986

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantSodium borohydrideHCID 4311764—
ReactantHCID 69546006HCID 69546006—
CatalystHCID 178418397HCID 178418397—
SolventIsopropanolHCID 3776—
SolventTetrahydrofuranHCID 8028—
ProductHCID 69546069HCID 6954606979.2%

Reaction Steps

To a solution of (1S-cis)-4-(di-tert-butoxycarbonylamino)cyclopent-2-enyl acetate (prepared as described by D. Zhang et.al. Tett. Lett. 1996, 3799–3802) (8.98 g), tetrakis(triphenylphosphine)palladium(0) (0.463 g) in isopropanol (135 ml) and tetrahydrofuran (135 ml) was added sodium borohydride (4.97 g) portionwise at 0° C. The mixture was stirred at 0° C. for 3 hours before the careful dropwise addition of glacial acetic acid (20 ml). The solution was concentrated in vacuo and the residue purified by chromatography (SiO2, diethylether 1:9 isohexane as eluent) to afford the sub-title compound (5.90 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07034032B2
Source datasetuspto-grants-2006_04
ORD IDord-ab3493598196468d8d2a5ed5a3d6aedb
Source noteuspto-grants-2006_04