Methanol → N-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]-N-methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine

HRID 2093341Notes

Reaction equation

HRID 2093341 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@@H:10]([N:15]([CH3:33])[C:16]2[CH:21]=[CH:20][N:19]=[C:18]3[N:22](COCC[Si](C)(C)C)[CH:23]=[CH:24][C:17]=23)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(Cl)Cl.CO.[OH-].[Na+]>O>[CH2:1]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@@H:10]([N:15]([CH3:33])[C:16]2[CH:21]=[CH:20][N:19]=[C:18]3[NH:22][CH:23]=[CH:24][C:17]=23)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 66662878N-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]-N-methyl-1-[2-(trimethylsilyl)-ethoxy]methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine

Product 1

HCID 66663007N-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]-N-methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amineYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-[(3R,4R)-1-benzyl-4-methylpiperidin-3-yl]-N-methyl-1-[2-(trimethylsilyl)ethoxy]methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine (0.065 g, 0.00014 mol) in trifluoroacetic acid (0.6 mL, 0.008 mol) and methylene chloride (3 mL, 0.05 mol) was stirred overnight. The solvent volume was reduced by roto-vap 3× azeotroped with MeOH. The resulting orange oil was stirred in methanol (1.5 mL, 0.037 mol) and 1.00 M of sodium hydroxide in water (0.5 mL) overnight. Solvents were removed under vacuum and the remaining solid was stirred in ethyl acetate and water. The organic phase was washed with sat. NaCl and the solvent was removed under vacuum to give 37 mg of an orange oil.

Workup

  1. customazeotroped with MeOH
  2. customSolvents were removed under vacuum
  3. washThe organic phase was washed with sat. NaCl
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-2e78ea53eebe42b6a93188930d67da81
Source dataset
uspto-grants-2013_05
Patent number
US08445488B2

Reaction notes

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