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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 243651Generated: October 25, 2026

Tert-butyl(5R)-2-(4-aminobenzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylate → Tert-butyl (2S,5R)-2-(4-aminobenzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylate

https://huagongshe.com/reaction/243651

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTert-butyl(5R)-2-(4-aminobenzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylateHCID 57907571—
SolventMethanolHCID 887—
ProductTert-butyl (2S,5R)-2-(4-aminobenzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylateHCID 57907438—

Reaction Steps

The intermediate i-3 (tert-butyl(5R)-2-(4-aminobenzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylate (4:1 mixture of cis and trans) was taken up in methanol and purified via the Berger Multigram SFC (supercritical) using an eluent of 30% methanol:60% carbon dioxide to separate the two diastereomers. The first isomer of the column was labeled minor isomer 1 and the second isomer was labeled major isomer 2.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08653260B2
Source datasetuspto-grants-2014_02
ORD IDord-49451e76ff3f4b09908adcaa370651e2
Source noteuspto-grants-2014_02