Tetrahydrofuran → benzyl (2R,4R)-4-hydroxy-2-methoxy-methyl-carbamoyl-pyrrolidine-1-carboxylate

HRID 13433Notes

Reaction equation

HRID 13433 reaction equation
[F-].[CH2:2]([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:24][C@H:25]1[CH2:29][N:28]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[C@@H:27]([C:40](=[O:45])[N:41](OC)C)[CH2:26]1)(C)(C)C.[O:58]1CCC[CH2:59]1>>[OH:24][C@H:25]1[CH2:29][N:28]([C:30]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[C@@:27]([C:40](=[O:45])[NH2:41])([O:58][CH3:59])[CH:26]1[CH3:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86619216benzyl (2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-2-(methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylate

Product 1

HCID 86619217benzyl (2R,4R)-4-hydroxy-2-methoxy-methyl-carbamoyl-pyrrolidine-1-carboxylate

Procedure

7.46 ml of tetrabutylammonium fluoride (1 M tetrahydrofuran solution) was added to a tetrahydrofuran (30 ml) solution of 2.04 g of benzyl (2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-2-(methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylate obtained in (step 2), and the reaction liquid was stirred at room temperature for 20 minutes. The solvent of the reaction liquid was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/3) to obtain the entitled compound.

Workup

  1. customobtained in (step 2)
  2. customthe reaction liquid
  3. customThe solvent of the reaction liquid
  4. customwas evaporated away under reduced pressure
  5. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/3)
  6. customto obtain the entitled compound

Sources & evidence

ORD record
ord-e7d48644d4c84c7a8f0afdd95ac4e7e9
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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