Methanol → HCID 11632828, compound

HRID 2114750Notes

Reaction equation

HRID 2114750 reaction equation
[BH4-].[Na+].CO.[CH3:5][O:6][C:7](=[O:32])[CH2:8][CH2:9][CH2:10][S:11][CH2:12][CH2:13][N:14]1[C@@H:19](/[CH:20]=[CH:21]/[C:22](=[O:30])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:18][CH2:17][CH2:16][C:15]1=[O:31]>C(Cl)Cl>[CH3:5][O:6][C:7](=[O:32])[CH2:8][CH2:9][CH2:10][S:11][CH2:12][CH2:13][N:14]1[C:15](=[O:31])[CH2:16][CH2:17][CH2:18][C@@H:19]1/[CH:20]=[CH:21]/[CH:22]([OH:30])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 66791198HCID 66791198, compound

Product 1

HCID 11632828HCID 11632828, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (1.0 mg, 0.026 mmol), followed by MeOH (0.1 mL), was added to a solution of 4-{2-[(R)-2-oxo-6-((E)-3-oxo-4-phenyl-but-1-enyl)-piperidin-1-yl]-ethylsulfanyl}-butyric acid methyl ester (6.8 mg, 0.017 mmol) in CH2Cl2 (0.3 mL) at 0 ° C. After 15 min at 0° C., the reaction was quenched with aqueous HCl (0.1 M, 4 mL) and extracted with CH2Cl2 (3×5 mL). The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo to afford 6.8 mg (99%) of the title compound.

Workup

  1. customthe reaction was quenched with aqueous HCl (0.1 M, 4 mL)
  2. extractionextracted with CH2Cl2 (3×5 mL)
  3. dry with materialThe combined organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-efce838837e44e1aa803fdc3faa1e985
Source dataset
uspto-grants-2008_10
Patent number
US07435746B2

Reaction notes

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