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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1691490Generated: October 27, 2026

Trifluoroacetic acid → (S)-methyl 5-(4-(benzyloxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

https://huagongshe.com/reaction/1691490

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
Reactantmethyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-oxo-5-{4-[(phenylmethyl)oxy]phenyl}pentanoateHCID 59164841—
SolventDichloromethaneHCID 6344—
Product(S)-methyl 5-(4-(benzyloxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylateHCID 5916483791%

Reaction Steps

To a solution of methyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-oxo-5-{4-[(phenylmethyl)oxy]phenyl}pentanoate (D2, 323 mg, 0.75 mmol) in dry DCM (4 ml) at 0° C., under nitrogen atmosphere was added trifluoroacetic acid (1 ml) dropwise. The resulting pale pink solution was allowed to warm to room temperature over 1 hour, then it was evaporated under reduced pressure, affording the title compound (D7, 291 mg, 0.68 mmol, 91%) as a greenish oil which may be used in the next step without any further purification; Rt (HPLC): 3.69 min; MS: (ES/+) m/z: 310 [MH+], C19H19NO3 requires 309.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08153681B2
Source datasetuspto-grants-2012_04
ORD IDord-cf36a5a7873149eb8d43411144ae3e33
Source noteuspto-grants-2012_04