Sodium Bicarbonate → 1,1-Dimethylethyl (2S)-4-[(6-amino-4-methyl-3-pyridinyl)methyl]-2-methyl-1-piperazinecarboxylate

HRID 534779Notes

Reaction equation

HRID 534779 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[C:4]([CH3:10])[CH:3]=1.[CH3:11][C@H:12]1[CH2:17][NH:16][CH2:15][CH2:14][N:13]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:16]2[CH2:15][CH2:14][N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:12]([CH3:11])[CH2:17]2)=[C:4]([CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylateHCID 552846706-Amino-4-methylnicotinaldehyde

Product 1

HCID 592621751,1-Dimethylethyl (2S)-4-[(6-amino-4-methyl-3-pyridinyl)methyl]-2-methyl-1-piperazinecarboxylateYield 53.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 6-amino-4-methyl-3-pyridinecarbaldehyde (D99) (0.053 g, 0.39 mmol), 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (0.117 g, 0.58 mmol) and sodium tri(acetoxy)borohydride (0.206 g, 0.97 mmol) in 1,2-DCE (10 mL) was sonicated to aid dissolution of the starting material then stirred at room temperature overnight. Saturated aqueous NaHCO3 (30 mL) was added and the mixture was stirred for 24 h. The reaction mixture was extracted with DCM (3×10 mL) and the organics were dried and concentrated to give the crude title compound as an oil (0.067 g) which was used in the next step without further purification. MS (ES): MH+ 321.3, MNa+ 343.3.

Workup

  1. customwas sonicated
  2. dissolutiondissolution of the starting material
  3. stirringthe mixture was stirred for 24 h
  4. extractionThe reaction mixture was extracted with DCM (3×10 mL)
  5. customthe organics were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-505e05e11a314995a538ac4309cf1836
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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