Benzyl chloroformate → HCID 19753252, compound

HRID 483645Notes

Reaction equation

HRID 483645 reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH2:11][CH2:10]2.[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.S([O-])(O)(=O)=O.[Na+]>CC(C)=O.O.C(OCC)(=O)C>[C:24]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH2:11][CH2:10]2)([O:23][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:25]

Participants

8

Reactant 4

HCID 10387Benzyl chloroformateHCID 90496Indan-5-amineHCID 516892Sodium BicarbonateHCID 516919Sodium Bisulfate

Product 1

HCID 19753252HCID 19753252, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium bicarbonate (7.20 g) is added to a solution of 5-aminoindan (XVA, 5.71 g) in acetone (60 ml) and water (30 ml) 0°, followed by the dropwise addition of benzylchloroformate (6.8 ml, 8.07 g) over 5 min. The mixture is stirred at 0° for about 1 hr, then at 20°-25° overnight. The mixture is poured into aqueous sodium hydrogen sulfate (10%, 200 ml), and ethyl acetate (300 ml). The organic extract is washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated under reduced pressure to give an oil. The oil is purified by column chromatography on 60-200 μsilica gel, eluting with ethyl acetate/hexane (10/90). The appropriate fractions are pooled and concentrated to give the title compound, mp 56°-59°; NMR (CDCl3, 300 MHz) 7.40-7.03, 7.11, 7.05, 6.65, 5.18, 2.85 and 2.05 δ; IR (mineral oil mull) 3275, 2925, 1693.5, 1544 and 1236 cm-1 ; MS (m/e) 267, 223, 222 and 91.

Workup

  1. customat 20°-25°
  2. customovernight
  3. extractionThe organic extract
  4. washis washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give an oil
  8. customThe oil is purified by column chromatography on 60-200 μsilica gel
  9. washeluting with ethyl acetate/hexane (10/90)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5149e3a916654eafa61716694bb57fad
Source dataset
uspto-grants-1993_07
Patent number
US05225565

Reaction notes

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