HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → cyclopropyl-(R)-pyrrolidin-2-yl-methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | N-(tert-Butoxycarbonyl)-D-prolinal | HCID 7009153 | — |
| Reactant | HCID 178478986 | HCID 178478986 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | cyclopropyl-(R)-pyrrolidin-2-yl-methanol | HCID 89726206 | 14.2% |
Reaction Steps
To a solution of (R)-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (200 mg, 1 mmol) in tetrahydrofuran at −78° C. was added a 1 M solution of cyclopropylmagnesium chloride (1.3 ml, 1.3 mmol). After stirring for 1 h at room temperature and addition of aqueous sodium hydrogencarbonate, extraction (3 times with dichloromethane), drying of the combined organic layers over sodium sulfate and evaporation of the solvents the crude product was heated with aqueous sodium hydroxide at 100° C. for 3 days to give 20 mg of crude cyclopropyl-(R)-pyrrolidin-2-yl-methanol which was used in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09284333B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-b3a64f72b9c64a8f830c6fa0cd48e8b3 |
| Source note | uspto-grants-2016_03 |