3-(tert-butyloxycarbonyl)-1-chloromethyl-5-nitro-1,2-dihydro-3H-benz[e]indole → HCID 10688060, compound

HRID 366826Notes

Reaction equation

HRID 366826 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([N+:17]([O-])=O)[C:13]3[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=3[C:11]=2[CH:10]([CH2:24][Cl:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.O=[Pt]=O>[NH2:17][C:14]1[C:13]2[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=2[C:11]2[CH:10]([CH2:24][Cl:25])[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[C:16]=2[CH:15]=1

Participants

4

Reactant 1

HCID 153804133-(tert-butyloxycarbonyl)-1-chloromethyl-5-nitro-1,2-dihydro-3H-benz[e]indole

Product 1

HCID 10688060HCID 10688060, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 13 (200 mg, 0.55 mmol) in THF (15 mL) was hydrogenated over PtO2 at 55 psi for 1.5 h. The catalyst was removed, the solvent was evaporated, and the resulting solid was triturated with petroleum ether to give 5-amino-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole (166 mg, 90%), mp >200° C. 1H NMR [(CD3)2SO] δ 8.01 (d, J=8.4 Hz, 1 H, H-6), 7.64 (d, J=8.3 Hz, 1 H, H-9), 7.45-7.25 (underlying br s, 1 H, H-4), 7.40 (t, J=7.4 Hz, 1 H, H-8), 7.20 (t, J=7.4 Hz, 1 H, H-7), 7.91 (s, 2 H, NH2), 4.11-3.87 (m, 4 H, H-1,2, CHHCl), 3.66 (dd, J=10.5, 8.3 Hz, 1 H, CHHCl), 1.53 (s, 9 H, C(CH3)3).

Workup

  1. customThe catalyst was removed
  2. customthe solvent was evaporated
  3. customthe resulting solid was triturated with petroleum ether

Sources & evidence

ORD record
ord-ad1a0a2768ec433699d212f66667eb7b
Source dataset
uspto-grants-2000_10
Patent number
US06130237

Reaction notes

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