Hydrazine → tert-butyl N-{[3-(aminomethyl)pyridin-2-yl]methyl}carbamate

HRID 2080280Notes

Reaction equation

HRID 2080280 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[C:14]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:15][CH:16]=[CH:17][CH:18]=1.NN>CO>[NH2:3][CH2:12][C:13]1[C:14]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 57542644Tert-butyl (3-((1,3-dioxoisoindolin-2-yl)methyl)pyridin-2-yl)methylcarbamate

Product 1

HCID 57542432tert-butyl N-{[3-(aminomethyl)pyridin-2-yl]methyl}carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (3-((1,3-dioxoisoindolin-2-yl)methyl)pyridin-2-yl)methylcarbamate (30 g, 81 mmol) in MeOH (450 mL) at 0° C. was added hydrazine (25 mL, 810 mmol). The mixture was allowed to warm to room temperature and stirred overnight. The precipitate was filtered off, and the filtrate was concentrated to dryness. The residue was triturated with dichloromethane (500 mL) and filtered. Concentration of the filtrate afforded tert-butyl (3-(aminomethyl)pyridin-2-yl)methylcarbamate in quantitative yield (18.7 g). LRMS (M+H+) m/z 238.1.

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was triturated with dichloromethane (500 mL)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-652c3a20af0743c78eab1170eaf21642
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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