Sodium borohydride → HCID 10868268, compound

HRID 1936564Notes

Reaction equation

HRID 1936564 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3=[CH:12][CH:13]=[CH:14][N:9]3[CH2:8][C:7](=[O:15])[C:6]=2[CH:16]=1.[BH4-].[Na+]>O1CCCC1.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3=[CH:12][CH:13]=[CH:14][N:9]3[CH2:8][CH:7]([OH:15])[C:6]=2[CH:16]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 10868191HCID 10868191, compound

Product 1

HCID 10868268HCID 10868268, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 9c (0.037 g 0.16 mmol) in dry tetrahydrofuran (0.5 ml) and dry methanol (0.7 ml), cooled to 0° C. under argon atmosphere, was added in portions sodium borohydride (0.09 g, 0.16 mmol). After stirring for 1 hour at 0° C. the reaction was quenched with a saturated solution of ammonium chloride (1 ml), the solvent was removed and the mixture was extracted with ethyl acetate (3×2 ml). The organic layers were dried and evaporated, the crude product was chromatographed (30% petroleum ether 40-60° in dichloromethane) to give 24c 0.036 g (96% yield). 1H NMR (CDCl3) δ7.40-7.33 (m, 1H); 7.24-7.18 (m, 1H); 6.93-6.84 (m, 2H); 6.33-6.31 (m, 1H); 6.11-6.08 (m, 1H); 5.12-5.04 (m, 1H); 4.91-4.83 (dd, 1H, J=14.22, 2.25 Hz); 4.34-4.24 (dd, 1H, J=14.02, 6.51 Hz); 2.09-2.04 (d, 1H, J=9.83 Hz).

Workup

  1. customwas quenched with a saturated solution of ammonium chloride (1 ml)
  2. customthe solvent was removed
  3. extractionthe mixture was extracted with ethyl acetate (3×2 ml)
  4. customThe organic layers were dried
  5. customevaporated
  6. customthe crude product was chromatographed (30% petroleum ether 40-60° in dichloromethane)

Sources & evidence

ORD record
ord-e4223f5c7bac49e4a7e90351c7c3d430
Source dataset
uspto-grants-2002_05
Patent number
US06391870B2

Reaction notes

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