Methyl 3-cyano-4-(isopropylsulfonyl)phenylcarbamate → Methyl 3-(aminomethyl)-4-(isopropylsulfonyl)phenylcarbamate

HRID 1667612Notes

Reaction equation

HRID 1667612 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16](=[O:19])[O:17][CH3:18])[CH:6]=[CH:7][C:8]=1[S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])#[N:2]>C1COCC1.[Ni]>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([NH:15][C:16](=[O:19])[O:17][CH3:18])[CH:6]=[CH:7][C:8]=1[S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10]

Participants

4

Reactant 1

HCID 57448208Methyl 3-cyano-4-(isopropylsulfonyl)phenylcarbamate

Product 1

HCID 57448210Methyl 3-(aminomethyl)-4-(isopropylsulfonyl)phenylcarbamateYield 96.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 15D (230 mg, 0.82 mmol) in THF (15 mL) was added Raney Ni (cat.) and the mixture was hydrogenated at 60 psi for 6 h. The reaction was filtered and concentrated to provide methyl 3-(aminomethyl)-4-(isopropylsulfonyl)phenylcarbamate (227 mg), which was suspended in ether. A solution of 4N HCl in dioxane (0.5 mL) was added and the reaction was concentrated to provide 15E (265 mg, 100%). LC-MS: 287.38 (M+H)+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8eda1e5cf32d4faba04f8fee09eb8097
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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