HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium diisopropylamide → (2R,4S)-N-allyloxycarbonyl-2-(2-oxoazetidin-3-ylmethyl)-4-tritylthiopyrrolidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | 1-(tert-Butyldimethylsilyl)azetidin-2-one | HCID 14068168 | — |
| Reactant | (2S,4S)-N-allyloxycarbonyl-2-iodomethyl-4-tritylthiopyrrolidine | HCID 57112975 | — |
| Product | (2R,4S)-N-allyloxycarbonyl-2-(2-oxoazetidin-3-ylmethyl)-4-tritylthiopyrrolidine | HCID 56992111 | 24.5% |
Reaction Steps
The same procedure as in Reference Example 22-1 was carried out by using N-tert-butyldimethylsilyl-2-oxoazetidine (650 mg, 3.5 mmol), lithium diisopropylamide (2.1M tetrahydrofuran solution, 3.34 ml, 7.0 mmol), and (2S,4S)-N-allyloxycarbonyl-2-iodomethyl-4-tritylthiopyrrolidine (1 g, 1.75 mmol) to obtain (2R,4S)-N-allyloxycarbonyl-2-(2-oxoazetidin-3-ylmethyl)-4-tritylthiopyrrolidine (220 mg, yield: 24%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05374720 |
| Source dataset | uspto-grants-1994_12 |
| ORD ID | ord-e17b1605f73a4b06ba6fc7eaf5e269f3 |
| Source note | uspto-grants-1994_12 |