Hydrochloric Acid → HCID 57287759, compound

HRID 1650280Notes

Reaction equation

HRID 1650280 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([N:12]([C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])[CH3:13])[CH2:9][C@H:8]1[CH2:20][O:21][Si](C(C)(C)C)(C)C)=[O:6])[CH:2]=[CH2:3].Cl.C(=O)([O-])O.[Na+].O>C(OCC)(=O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([N:12]([C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])[CH3:13])[CH2:9][C@H:8]1[CH2:20][OH:21])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 18639181HCID 18639181, compound

Product 1

HCID 57287759HCID 57287759, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4S)-1-allyloxycarbonyl-4-(N-allyloxycarbonyl-N-methylamino)-2-t-butyldimethylsilyloxymethylpyrrolidine (3.73 g) in ethyl acetate (100 ml) was added 12N hydrochloric acid (0.82 ml) at ambient temperature. After stirring at ambient temperature for 30 minutes, to the mixture were added sodium hydrogen carbonate (1.90 g) and cold water (100 ml). The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (100 ml) eluting with a mixture of n-hexane and ethyl acetate (7:3-2:8 V/V) to give (2S,4S)-1-allyloxycarbonyl-4-(N-allyloxycarbonyl-N-methylamino)-2-hydroxymethylpyrrolidine (2.04 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (100 ml)
  6. washeluting with a mixture of n-hexane and ethyl acetate (7:3-2:8 V/V)

Sources & evidence

ORD record
ord-45569b7738704d8a864c9e7e2ea33d38
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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