Hydrochloric Acid → HCID 12132857, compound

HRID 22972Notes

Reaction equation

HRID 22972 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][O:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][N:11]1[C@@H:15](/[CH:16]=[CH:17]/[C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][C:12]1=[O:25])[CH3:2].[BH4-].[Na+].Cl.C(OCC)(=O)C>C(O)C.CO>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][O:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][N:11]1[C:12](=[O:25])[CH2:13][CH2:14][C@@H:15]1/[CH:16]=[CH:17]/[CH:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 12132856{(Z)-4-[(R)-2-oxo-5-((E)-3-oxo-oct-1-enyl)-pyrrolidin-1-yl]-but-2-enyloxy}-acetic acid ethyl ester

Product 1

HCID 12132857HCID 12132857, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of {(Z)-4-[(R)-2-oxo-5-((E)-3-oxo-oct-1-enyl)-pyrrolidin-1-yl]-but-2-enyloxy}-acetic acid ethyl ester (0.7 g, 1.97 mmol) in 15 mL of ethanol was stirred at 0° C., and 0.082 g NaBH4 was added. The reaction was allowed to come to room temperature and stirred for 7 hours, followed by addition of a solution of hydrochloric acid in methanol (2 M, 1-2 mL) and extraction with ethyl acetate. The organic phase was dried, concentrated, purified via chromatography to yield {(Z)-4-[(R)-2-((E)-3-hydroxy-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-but-2-enyloxy}-acetic acid ethyl ester, and taken directly on to the next step.

Workup

  1. customto come to room temperature
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. custompurified via chromatography

Sources & evidence

ORD record
ord-838f866032fa4434bfae13020c704090
Source dataset
uspto-grants-2005_02
Patent number
US06849657B2

Reaction notes

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