Isopropanol → HCID 9923422, compound

HRID 2300583Notes

Reaction equation

HRID 2300583 reaction equation
[OH:1][C:2]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[C:7]2[C:3]=1[C:4]([CH3:18])([CH3:17])[C:5](=[O:16])[N:6]=2.[BH4-].[Na+].[CH3:21][C:22](OC(C)=O)=[O:23].[CH3:28][CH:29]([OH:31])C>>[C:22]([O:11][C:10]1[C:2]([O:1][C:29](=[O:31])[CH3:28])=[C:3]2[C:7](=[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=13)[NH:6][C:5](=[O:16])[C:4]2([CH3:18])[CH3:17])(=[O:23])[CH3:21]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 7918Acetic AnhydrideHCID 4311764Sodium borohydride2×HCID 178429195HCID 178429195, compound

Product 1

HCID 9923422HCID 9923422, compound

Procedure

To a solution of 4-hydroxy-3,3-dimethyl-2H-benzo[g]indole-2,5(3H)-dione (0.030 g, 0.124 mmol) in i-PrOH (0.5 mL) was added NaBH4 (0.020 g, 0.52 mmol) while stirring at RT. After 5 minutes, Ac2O (100 μL, 0.1 g, 0,98 mmol) was added via a syringe and the mixture was allowed to stir for 1 h followed by addition of more NaBH4 (0.020 g, 0.52 mmol) and stirring over night. The solvent was removed in vacuum and the solid was dissolved in CHCl3, filtered and purified by prep. HPLC (RP). Yield: 0.016 mg (40%). 1H NMR (400 MHz, CDCl3) δ 1.50 (brs, 6 H), 2.35 (appd, 6 H), 7.47 (m, 2 H), 7.68 (d, 1 H), 7.85 (d, 1 H), 10.05 (brs, 1 H). MS (CI) m/z: 328.36 (M+1).

Workup

  1. stirringto stir for 1 h
  2. stirringstirring over night
  3. customThe solvent was removed in vacuum
  4. dissolutionthe solid was dissolved in CHCl3
  5. filtrationfiltered
  6. custompurified by prep

Sources & evidence

ORD record
ord-14387e86c435441db9be4851a6b64a4a
Source dataset
uspto-grants-2002_12
Patent number
US06498182B2

Reaction notes

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