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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1158356Generated: October 25, 2026

Acetonitrile → (3S,4R)-3-Hydroxymethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

https://huagongshe.com/reaction/1158356

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetonitrileHCID 6342—
ReactantTetrabutylammonium Fluoride TrihydrateHCID 11726816—
ReactantAcetonitrile--water (1/1)HCID 18373917—
Reactant(3S*,4R*)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 131728362—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
Product(3S,4R)-3-Hydroxymethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 59512299—

Reaction Steps

The title compound is prepared in a similar manner as described for Example 9/reaction step H, from (3S*,4R*)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (25.0 g, 41.1 mmol) and tetrabutylammonium fluoride trihydrate (19.4 g, 61.6 mmol) in THF (150 mL) as a colorless oil. MS: 495.2 [M+H]+; tR (HPLC, C18 column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/1.5 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 4.84 min.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07807709B2
Source datasetuspto-grants-2010_10
ORD IDord-673a6965d32c432096f40f8fabbd137e
Source noteuspto-grants-2010_10