Hydrochloric Acid → HCID 66884695, compound

HRID 1582219Notes

Reaction equation

HRID 1582219 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5](=[O:30])[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[CH2:15][CH2:14][C@@H:13]1/[CH:18]=[CH:19]/[C:20](=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1.Cl>C(Cl)Cl.CO>[CH3:3][O:4][C:5](=[O:30])[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[CH2:15][CH2:14][C@@H:13]1/[CH:18]=[CH:19]/[CH:20]([OH:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10069989HCID 10069989, compound

Product 1

HCID 66884695HCID 66884695, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (4.3 mg, 0.11 mmol) was added to a solution of (4-{(R)-2-[(E)-4-(3-chlorophenyl)-3-oxo-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-butoxy)-acetic acid methyl ester (42 mg, 0.10 mmol) in CH2Cl2 (1 mL) at 0° C. Methanol (3 drops) was added and the reaction was stirred at rt for 3 h. Aqueous HCl (0.5 M, 5 mL) was added and the mixture was extracted with CH2Cl2 (3×5 mL). The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (0%→5% MeOH/CH2Cl2) to afford 31 mg (73%) of (4-{(R)-2-[(E)-4-(3-chlorophenyl)-3-hydroxy-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-butoxy)-acetic acid methyl ester.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×5 mL)
  2. dry with materialThe combined organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (0%→5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-eabcf8fcb89b47298cff980987c56d9f
Source dataset
uspto-grants-2004_05
Patent number
US06734206B1

Reaction notes

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