Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | alpha-Chloro-m-nitrotoluene | HCID 12078 | — |
| Reactant | (3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine | HCID 1514397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86603710 | HCID 86603710 | 97.5% |
Reaction Steps
To a mixture of tert-butyl (3R)-3-pyrrolidinylcarbamate (450 mg), 1-(chloromethyl)-3-nitrobenzene (435 mg) in DMF (4.5 mL) was added N,N-diisopropylamine (463 uL), which was stirred at 75° C. for 4 hours. To the resultant was added H2O. The mixture was extracted with ethyl acetate. The organic phase was washed brine, dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give tert-butyl [(3R)-1-(3-nitrobenzyl)-3-pyrrolidinyl]carbamate (, 757 mg) as a orange oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07465731B2 |
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| Source dataset | uspto-grants-2008_12 |
|---|
| ORD ID | ord-7466fe41217849939807fb414d297497 |
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| Source note | uspto-grants-2008_12 |
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