Ethyl bromoacetate → 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-ethoxycarbonylmethoxy-1H-indene

HRID 1741375Notes

Reaction equation

HRID 1741375 reaction equation
[CH3:1][N:2]([CH:21]1[C:29]2[C:24](=[C:25]([OH:30])[CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1)[CH2:3][C:4]1[O:5][C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1.Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][N:2]([CH:21]1[C:29]2[C:24](=[C:25]([O:30][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1)[CH2:3][C:4]1[O:5][C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:8]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 183672371-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-hydroxy-1H-indene

Product 1

HCID 183673111-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-ethoxycarbonylmethoxy-1H-indeneYield 60.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[N-methyl-N-[(4,5-diphenyloxazol-9-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (109 mg) in dichloromethane (2 ml) was added 1M boron tribromide dichloromethane solution (1 ml) at 0° C. After being stirred for 4 hours at 0° C., the solvent was evaporated in vacuo. The residue was extracted with ethyl acetate. The mixture was washed with brine, dried over MgSO4 and evaporated in vacuo to afford crude 1-[N-methyl-N-[4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-hydroxy-1H-indene (109 mg). To a solution of crude 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-hydroxy-1H-indene (109 mg) and ethyl bromoacetate (80 mg) in DMF (3 ml) was added K2CO3 (80 mg). After being stirred for 24 hours, the solution was extracted with ethyl acetate. The mixture was washed with brine, dried over MgSO4 and evaporated on vacuo. The residue was purified by chromatography on silica gel to afford 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-ethoxycarbonylmethoxy-1H-indene (80 mg) MS (m/z): 483 (M+ +1) NMR (CDCl3, δ): 1.29 (3H, t, J=7.1 Hz), 1.98-2.21 (2H, m), 2.41 (3H, s), 2.75-3.18 (2H, m), 3.78 (1H, d, J=12 Hz), 3.82 (1H, d, J=12 Hz), 4.25 (2H, q, J=7.1 Hz), 4.63 (2H, s), 4.55-4.65 (1H, m), 6.62 (1H, m), 7.15-7.18 (2H, m), 7.25-7.45 (6H, m), 7.60-7.75 (4H, m)

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe mixture was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated on vacuo
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e552b5adf36f4d9a89cd73b65f5ead74
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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