Sodium borohydride → HCID 22562027, compound

HRID 1839615Notes

Reaction equation

HRID 1839615 reaction equation
[BH4-].[Na+].C[O:4][C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][C:16](=[O:22])[NH:17]3)[CH:8]=1.[Cl-].[Cl-].[Ca+2]>O.CO.C1COCC1>[OH:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][C:16](=[O:22])[NH:17]3)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 20761750HCID 20761750, compound

Product 1

HCID 22562027HCID 22562027, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a suspension of NaBH4 (600 mg, 16 mmol) in 15% H2O/MeOH (6 mL) under nitrogen at rt was added dropwise a solution of [3-(2-oxo-2,3-dihydro-1H-indol-4-yl)-phenyl]-acetic acid methyl ester (450 mg, 1.6 mmol) in THF (3 mL). After stirring at rt for overnight, to the reaction was added CaCl2 (300 mg) and stirring was continued for another 5 hours. The reaction was quenched with acetic acid (2 mL), concentrated, diluted with ethyl acetate, washed with 0.5 N HCl (3×15 mL), 10% NaHCO3 (3×15 mL), brine (1×), dried and concentrated. The oily residue was purified to give 384 mg (95%) of 4-[3-(2-hydroxy-ethyl)-phenyl]-1,3-dihydro-indol-2-one.

Workup

  1. stirringstirring
  2. waitwas continued for another 5 hours
  3. customThe reaction was quenched with acetic acid (2 mL)
  4. concentrationconcentrated
  5. additiondiluted with ethyl acetate
  6. washwashed with 0.5 N HCl (3×15 mL), 10% NaHCO3 (3×15 mL), brine (1×)
  7. customdried
  8. concentrationconcentrated
  9. customThe oily residue was purified

Sources & evidence

ORD record
ord-4e2211ac643a474095d6a96b98b10a71
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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