1-Methyl-4-piperidone → HCID 66755285, compound

HRID 1631982Notes

Reaction equation

HRID 1631982 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:14][N:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1>C1COCC1>[C:4]([O:3][C:1]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][CH:18]2[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]2)[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 740491-Methyl-4-piperidone2×HCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

Product 1

HCID 66755285HCID 66755285, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-(−)-N-Boc-3-aminopyrrolidine (500 mg, 2.68 mmol) and 1-methyl-4-piperidone (0.34 mL, 2.95 mmol) in THF (10 mL) MP-(OAc)3BH resin (Argonaut; 2.55 mmol/g; 2.63 g, 6.71 mmol) was added and the reaction mixture was agitated at room temperature for 18 hours. Then, 1-methyl-4-piperidone (0.28 mL, 2.42 mmol) was added and the reaction mixture was agitated for 24 hours more. The reaction mixture was filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using 12% MeOH in CH2Cl2 as eluent to afford (S)-3-(1-methyl-piperidin-4-ylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester (750 mg, 99%) as an orange oil.

Workup

  1. stirringthe reaction mixture was agitated for 24 hours more
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel using 12% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-97b8cb9dc513457b9b1a43173fb38837
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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