HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrabutylammonium Fluoride → (3R,4S)-3-({[4-Ethyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | (3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-({[4-ethyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 131728364 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | (3R,4S)-3-({[4-Ethyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 68618170 | — |
Reaction Steps
From (3S,4R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-({[4-ethyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (13.1 g, 21.6 mmol) and TBAF (17 g, 54 mmol), and purification by flash chromatography on silica gel (CH2Cl2/MeOH 95:5) to give the title compound as yellow oil. TLC, Rf (AcOEt)=0.4,MS (LC-MS): 437.3 [M+H-tBu]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 6.74 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07807709B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-cca118e06c3b4ce78594b38261152421 |
| Source note | uspto-grants-2010_10 |