HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isobutane → (3S,4R)-3-Hydroxymethyl-4-({isopropyl-[1-(3-methoxy-propyl)-1H-indole-6-carbonyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isobutane | HCID 6360 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Reactant | tert-butyl (3S,4R)-3-(2-tert-butylsilyloxypropan-2-yl)-4-[[[1-(3-methoxypropyl)indole-6-carbonyl]-propan-2-ylamino]methyl]pyrrolidine-1-carboxylate | HCID 178495133 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Ethylacetate methanol | HCID 21584119 | — |
| Product | (3S,4R)-3-Hydroxymethyl-4-({isopropyl-[1-(3-methoxy-propyl)-1H-indole-6-carbonyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 68630543 | — |
Reaction Steps
From (3S,4R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-({isopropyl-[1-(3-methoxy-propyl)-1H-indole-6-carbonyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (6.79 g, 11.3 mmol) and TBAF (5.35 g, 17.0 mmol) and purification by flash chromatography on silivca gel (chexane/AcOEt 50:50 to 0:100 to AcOEt/MeOH 90:10). TLC, Rf (AcOEt)=0.34. MS (LC-MS): 432 [M+H-tBu]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/15 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 5.73 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07807709B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-58673269bf03418fa2e1db8a0b4a8a99 |
| Source note | uspto-grants-2010_10 |