1-Methyl-4-piperidone → HCID 66755114, compound

HRID 1643967Notes

Reaction equation

HRID 1643967 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.[CH3:15][N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1>C1COCC1>[C:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][C@H:3]([CH2:2][NH:1][CH:19]2[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]2)[CH2:4]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 740491-Methyl-4-piperidoneHCID 1515152tert-Butyl (3R)-3-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 66755114HCID 66755114, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-3-(aminomethyl)-1-N-Boc-pyrrolidine (252 mg, 1.26 mmol) and 1-methyl-4-piperidone (0.16 mL, 1.38 mmol) in THF (10 mL) MP-(OAc)3BH resin (Argonaut; 2.33 mmol/g; 1.35 g, 3.15 mmol) was added and the reaction mixture was agitated at room temperature for 24 hours. Then, the reaction mixture was filtered and concentrated in vacuo to afford (R)-3-[(1-methyl-piperidin-4-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (370 mg, 99%) as an orange oil. The product was used without further purification.

Workup

  1. filtrationThen, the reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-352b04c18671464b9d165daaa5fb7454
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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