Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- | HCID 85083 | — |
| Reactant | tert-butyl N-(4-oxocyclohexyl)carbamate | HCID 1512535 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 86635872 | HCID 86635872 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67413125 | HCID 67413125 | 57.1% |
Reaction Steps
To prepare compound 2 of Scheme 7-1, tert-Butyl 4-oxocyclohexylcarbamate (9.0 g, 42.5 mmol) was treated with HCl (4N in 1,4-dioxane, 60 mL) at rt. After 4 h stirring, the reaction was concentrated to obtain the crude product (6.3 g), which was dissolved in anhydrous DMF (200 mL). N-Boc-L-Pro-OH (9.1 g, 42.3 mmol)), HATU (17.7 g, 46.6 mmol) and DIEA (22.8 mL, 131 mmol) were added at rt. After stirring overnight, the reaction was quenched by brine, extracted by ethyl acetate. The combined organic phases were washed with brine and H2O, dried with Na2SO4. After removal of the solvents, the crude product was purified by silica gel column chromatography (ethyl acetate) to afford (S)-tert-butyl 2-(4-oxocyclohexylcarbamoyl)pyrrolidine-1-carboxylate (7.5 g, 57% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09120779B2 |
|---|
| Source dataset | uspto-grants-2015_09 |
|---|
| ORD ID | ord-8577e0db00cf4559b7b6e45a9cac4501 |
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| Source note | uspto-grants-2015_09 |
|---|
