Sodium borohydride → HCID 86755708, compound

HRID 1873157Notes

Reaction equation

HRID 1873157 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5](=[O:21])[C@@H:6]([OH:20])[CH2:7][CH2:8][N:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:19]>C1COCC1.O>[OH:20][CH:6]([CH2:7][CH2:8][N:9]1[C@@H:17]([OH:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:19])[C:5]([O:4][CH3:3])=[O:21]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14683717HCID 14683717, compound

Product 1

HCID 86755708HCID 86755708, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Sodium borohydride (0.474 g, 12.54 mmol) was added portionwise to a -20° C., stirred solution of (s)-(+)-α-hydroxy-1,3-dioxo-2-isoindolinebutyric acid methyl ester (3.0 g, 11.4 mmol) in THF/water (30/1.38 mL) for 6 hours. Upon cooling to room temperature, the reaction mixture was carefully quenched and acidified with 10% aqueous HCl. Aqueous mixture was extracted with ethyl acetate (300 mL). The ethyl acetate extract was washed with water and brine. Silica gel (15 mL) was added. Solvents were removed and the silica adsorbate was flash chromatographed (eluent 95: 5 petroleum ether: dichloromethane) to provide the title compound as an oil (0.96 g, 32%): MS (EI): [M+], 265.

Workup

  1. customthe reaction mixture was carefully quenched
  2. extractionAqueous mixture was extracted with ethyl acetate (300 mL)
  3. extractionThe ethyl acetate extract
  4. washwas washed with water and brine
  5. additionSilica gel (15 mL) was added
  6. customSolvents were removed
  7. customchromatographed (eluent 95: 5 petroleum ether: dichloromethane)

Sources & evidence

ORD record
ord-bc2b4743125d4c68ac25fdb12a933b3c
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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