Hydrochloric Acid → HCID 66884852, compound

HRID 1582217Notes

Reaction equation

HRID 1582217 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[CH2:18][CH2:19][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[CH2:18][CH2:19][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 66884727HCID 66884727, compound

Product 1

HCID 66884852HCID 66884852, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (4.1 mg, 0.11 mmol) was added to a solution of (4{(R)-2-[4-(3-Chlorophenyl)-3-oxo-butyl]-5-oxo-pyrrolidin-1-yl}-butoxy)-acetic acid methyl ester (44 mg, 0.11 mmol) in CH2Cl2 (1 mL) at rt. Methanol (3 drops) was added and the reaction was stirred at rt for 4.5 h. Aqueous HCl (0.5 M, 5 mL) was added and the mixture was extracted with CH2Cl2 (2×8 mL). The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (0%→3% MeOH/CH2Cl2) to afford 9.1 mg (21%) of (4-{(R)-2-[4-(3-chlorophenyl)-3-hydroxy-butyl]-5-oxo-pyrrolidin-1-yl}-butoxy)-acetic acid methyl ester.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (2×8 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%→3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7cae722d70d7432c9227f096ede84d27
Source dataset
uspto-grants-2004_05
Patent number
US06734206B1

Reaction notes

Loading…