HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diazomethane → (2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diazomethane | HCID 9550 | — |
| Reactant | (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid | HCID 88804 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester | HCID 2734883 | 96.1% |
Reaction Steps
To a solution of compound 235 (5.2 g, 22.49 mmol) in THF (50 mL) was added diazomethane (38.5 mL, 27.0 mmol, 0.7M) dropwise until yellow color persists. The mixture was concentrated to afford title compound 236 (5.3 g, 96%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ (ppm): 4.50-4.47 (m, 1H), 4.44 (t, J=7.7 Hz, 1H), 3.76-3.43 (m, 2H), 3.73 (s, 3H), 2.33-2.22 (m, 1H), 2.11-2.03 (m, 1H), 1.91 (m, 1H), 1.45-1.41 (m, 9H). LRMS (ESI): (calc.) 245.13 (found) 146.0 (M-Boc+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08399452B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-04e80402818f4dfa988ba73d054500b0 |
| Source note | uspto-grants-2013_03 |