Hydrazine → HCID 21912822, compound

HRID 1245597Notes

Reaction equation

HRID 1245597 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[CH:15]([CH3:20])[C:16](=O)[O:17]C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:22][NH2:23]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:23][NH:22][C:16](=[O:17])[C:15]=2[CH3:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 21912726HCID 21912726, compound

Product 1

HCID 21912822HCID 21912822, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 419 mg (1.4 mmol) of 1-(tert-butoxycarbonyl)-4-(1,3-dioxo-3-methoxy-2-methyl-prop-1-yl)piperidine (from Step B) and 0.26 mL (8.4 mmol) of hydrazine in 5 mL of toluene was refluxed for 50 minutes. The reaction was cooled to rt and placed in the freezer overnight. After decanting the solvent, the white solid was triturated with Et2O to provide the title compound, which was used without further purification. 1H-NMR (500 MHz) δ 1.49 (s, 9H), 1.55–1.63 (m, 2H), 1.77–1.79 (m, 2H), 1.90 (s, 3H), 2.69–2.77 (m, 3H), 4.22 (m, 2H), 5.15–5.79 (br m, 2H).

Workup

  1. customplaced in the freezer overnight
  2. customAfter decanting the solvent
  3. customthe white solid was triturated with Et2O

Sources & evidence

ORD record
ord-acca46599e064ab5b1b2484cec7067c1
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

Loading…