HuagongsheHuagongshe Chemistry Print Report · For research reference only
Glyceraldehyde → (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-(2,3-dihydroxyprop-1-yl)pyrrolidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Glyceraldehyde | HCID 751 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine | HCID 22842874 | — |
| Reactant | (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-butylpyrrolidine | HCID 53802070 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-(2,3-dihydroxyprop-1-yl)pyrrolidine | HCID 54393635 | 72% |
Reaction Steps
The title compound was synthesized as described for compound 10 using (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine (Compound 1) (0.5 g, 1.2 mmol), methanol (30 ml), glyceraldehyde (0.134 g, 1.5 mmol) and sodium cyanoborohydride (0.094 g, 1.5 mmol). Purification of the crude product on silica gel (Eluent: Ethyl acetate) afforded (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-(2,3-dihydroxyprop-1-yl)pyrrolidine (0.424 g, yield: 72%) as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06451836B1 |
| Source dataset | uspto-grants-2002_09 |
| ORD ID | ord-fd1226dda6004ccc8fbddd8f7288a53b |
| Source note | uspto-grants-2002_09 |