p-Toluenesulfonic acid → HCID 18367319, compound

HRID 1741412Notes

Reaction equation

HRID 1741412 reaction equation
[NH2:1][CH:2]1[C:10]2[C:5](=[C:6]([O:11][CH3:12])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[OH:13][CH2:14][CH2:15][CH2:16][C:17]([C:19]1[O:20][C:21]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:23]=1)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[OH:13][CH2:14][CH2:15][CH2:16][CH:17]([NH:1][CH:2]1[C:10]2[C:5](=[C:6]([O:11][CH3:12])[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1)[C:19]1[O:20][C:21]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:23]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 30167414-Methoxy-2,3-dihydro-1H-inden-1-amineHCID 18367218HCID 18367218, compound

Product 1

HCID 18367319HCID 18367319, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-amino-2,3-dihydro-4-methoxy-1H-indene (0.30 g), 4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butan-1-one (0.56 g) and p-toluenesulfonic acid (catalytic amount) in toluene (50 ml) was refluxed for 2 days with Dean-stark equipment. The solvent was evaporated in vacuo and the residue was dissolved in methanol (10 ml). To the methanol solution was added NaBH4 (0.20 g) at 0° C. After being stirred for 1 hour at the same temperature, the solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate and sat. NaHCO3. The organic layer was washed with brine. The dried solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give 1-[[4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butyl]amino]-2,3-dihydro-4-methoxy-1H-indene (0.27 g). MS (m/z): 455 (M+ +1) NMR (CDCl3, δ): 1.60-3.20 (10H, m), 3.76 (2.5H, s), 3.84 (3.5H, s), 4.02-4.52 (2H, m), 7.59-7.69 (4H, m), 6.69-7.39 (9H, m)

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in methanol (10 ml)
  3. additionTo the methanol solution was added NaBH4 (0.20 g) at 0° C
  4. customthe solvent was evaporated in vacuo
  5. customthe residue was partitioned between ethyl acetate and sat. NaHCO3
  6. washThe organic layer was washed with brine
  7. customThe dried solvent was evaporated in vacuo
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a03feda6e4fd4a759932c5ed4649774d
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

Loading…