HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium borohydride → (2R,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 1,2-Pyrrolidinedicarboxylic acid, 4-[(methylsulfonyl)oxy]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,4R)- | HCID 10782162 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (2R,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol | HCID 53830029 | 83.4% |
Reaction Steps
To a solution of (2R,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxy-2-methoxycarbonylpyrrolidine (11.21 g: 34.4 mmole) in a mixture of tetrahydrofuran (34 ml) and ethanol (51 ml), sodium borohydride (5.21 g: 137.7 mmole) is added in a nitrogen atmosphere under ice cooling. The mixture is stirred for 75 minutes at room temperature to give (2R,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (8.47 g). Yield: 83%. Colorless crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05703243 |
| Source dataset | uspto-grants-1997_12 |
| ORD ID | ord-9d9ed2e5ab12401ca5ba189a69491bac |
| Source note | uspto-grants-1997_12 |