Methylhydrazine → HCID 86724082, compound

HRID 1748740Notes

Reaction equation

HRID 1748740 reaction equation
[C:1]([CH2:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=O)#[N:2].[CH3:18][NH:19][NH2:20]>CCO>[NH2:2][C:1]1[N:19]([CH3:18])[N:20]=[C:4]([C@@H:6]2[CH2:10][CH2:9][CH2:8][N:7]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:3]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 73424848HCID 73424848, compound

Product 1

HCID 86724082HCID 86724082, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl (2S)-2-(2-cyanoacetyl)pyrrolidine-1-carboxylate (5.8 g, 24.3 mmol), was dissolved in EtOH (100 mL). Methylhydrazine (1.8 mL, 35 mmol) was added and the resulting mixture was heated, for about 12 h, at about 80° C. After cooling to rt, the mixture was concentrated in vacuo. The residue was taken up in toluene (50 mL) and stirred overnight. The precipitated solid was collected by filtration and washed with toluene (2 mL) and diethyl ether to afford tert-butyl (2S)-2-(5-amino-1-methyl-pyrazol-3-yl)pyrrolidine-1-carboxylate (4.43 g, 16.3 mmol, 68%), as white solid: 1H-NMR (CDCl3, Bruker 400 MHz, rotamers) δ 1.35 and 1.45 (9 H, br. s), 1.70-2.24 (4 H, m), 3.36-3.53 (4 H, m), 3.60 (3 H, br s), 4.70-4.78 and 4.83-4.90 (1 H, m), 5.35 and 5.41 (1H, br s).

Workup

  1. temperatureAfter cooling to rt
  2. concentrationthe mixture was concentrated in vacuo
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with toluene (2 mL) and diethyl ether

Sources & evidence

ORD record
ord-cbdd238a20544f028dcefa3f14fea561
Source dataset
uspto-grants-2015_10
Patent number
US09150592B2

Reaction notes

Loading…