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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1526019Generated: November 2, 2026

Trifluoroacetic acid → HCID 68671068, compound

https://huagongshe.com/reaction/1526019

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantTetrahydro-4H-pyran-4-oneHCID 121599—
ReactantHCID 68671314HCID 68671314—
SolventDichloromethaneHCID 6344—
ProductHCID 68671068HCID 6867106888.5%

Reaction Steps

Tert-butyl 2-amino-4-{[(2S)-1-methylpyrrolidin-2-yl]methoxy}benzoate (400 mg, 1.3 mmol) was dissolved in 20 ml of DCM under argon atmosphere. Tetrahydro-4H-pyran-4-one (0.19 ml, 2.05 mmol), TFA (0.29 ml, 3.69 mmol) and Me4BH(OAc)3, (540 mg, 2.05 mmol) were added. The resulting slurry was stirred overnight at room temperature then quenched with 15 ml of NaHCO3 10% and extracted twice with 20 ml of DCM. The organic layers were then dried over Na2SO4, filtered off and concentrated to yield a yellow oil (448 mg, 1.15 mmol, 88%) which was used in the next step without any further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09085558B2
Source datasetuspto-grants-2015_07
ORD IDord-dad3feeece1f4dd982c783a9c4e9edf8
Source noteuspto-grants-2015_07