Water → HCID 57145713, compound

HRID 975657Notes

Reaction equation

HRID 975657 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si](C(C)(C)C)(C)C)[CH2:9][C@H:8]1[CH2:20][N:21]1[CH2:26][CH2:25][N:24]([CH:27]=[O:28])[CH2:23][C:22]1=[O:29])=[O:6])[CH:2]=[CH2:3].O>O1CCCC1>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:20][N:21]1[CH2:26][CH2:25][N:24]([CH:27]=[O:28])[CH2:23][C:22]1=[O:29])=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 962WaterHCID 54016814HCID 54016814, compound

Product 1

HCID 57145713HCID 57145713, compoundYield 132.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-1-allyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(4-formyl-2-oxopiperazin-1-yl) methylpyrrolidine (11.74 g) in tetrahydrofuran (100 ml) was added n-tetrabutylammonium fluoride under ice cooing with stirring, and the mixture was stirred at the same temperature for 1 hour. Water was added to the mixture, and the mixture was evaporated in vacuo. Ethanol was added to the residue, and the mixture was stirred at 60° C. for 20 minutes. The mixture was filtered, and the filtrate was evaporated in vacuo. The residue was purified by silica gel chromatography eluting with a mixture of chloroform and methanol (9:1 v/v) to give (2S,4R)-1-allyloxycarbonyl-2-(4-formyl-2-oxo-piperazin-1-yl) methyl-4-hydroxypyrrolidine (11.38 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. customthe mixture was evaporated in vacuo
  3. additionEthanol was added to the residue
  4. stirringthe mixture was stirred at 60° C. for 20 minutes
  5. filtrationThe mixture was filtered
  6. customthe filtrate was evaporated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with a mixture of chloroform and methanol (9:1 v/v)

Sources & evidence

ORD record
ord-1d8f0cde768e400eb27fe6e789168d8e
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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