Water → tert-butyl (3S)-3-methyl-4-(6-nitropyridin-3-yl)piperazine-1-carboxylate

HRID 1185035Notes

Reaction equation

HRID 1185035 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][NH:27][C@@H:26]([CH3:30])[CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].O>CS(C)=O>[CH3:30][C@@H:26]1[N:27]([C:2]2[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:28][CH2:29][N:24]([C:22]([O:21][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:23])[CH2:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 8176205-Bromo-2-nitropyridineHCID 7023035(S)-1-Boc-3-methylpiperazine

Product 1

HCID 86683728tert-butyl (3S)-3-methyl-4-(6-nitropyridin-3-yl)piperazine-1-carboxylateYield 50%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

Into a solution of 5-bromo-2-nitropyridine (30 g, 148 mmol) in DMSO (350 mL) were added K2CO3 (14 g, 104 mmol) and (3S)-tert-butyl-3-methylpiperazine-1-carboxylate (10.0 g, 50 mmol). The mixture was stirred at 65° C. overnight and then after cooling to room temperature, poured into water (700 mL). The solid precipitate was collected and dried under vacuum. It was further purified on a flash column eluting with 20:1 petroleum ether/ethyl acetate and then with CH2Cl2 to give 105a as a yellow solid (8.05 g, 50%). LCMS: [M+H]+ 323

Workup

  1. temperatureafter cooling to room temperature
  2. customThe solid precipitate was collected
  3. customdried under vacuum
  4. customIt was further purified on a flash column
  5. washeluting with 20:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-354059ca8d3d4b78a2f1625c043e6f9f
Source dataset
uspto-grants-2014_03
Patent number
US08669251B2

Reaction notes

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