Hydrochloric Acid → HCID 23090152, compound

HRID 1366532Notes

Reaction equation

HRID 1366532 reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:7][CH2:6][N:5](CC2C=CC=CC=2)[C:4]1([CH3:16])[CH3:15].Cl>CO.[Pd]>[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:7][CH2:6][NH:5][C:4]1([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66936307HCID 66936307, compound

Product 1

HCID 23090152HCID 23090152, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of racemic N,N,2,2-tetramethyl-1-(phenylmethyl)-3-pyrrolidinamine (0.5637 g, 2.426 mmol) in MeOH (24 mL) was added 1 N aq. HCl (4.9 ml) and 10% Pd/C (50% water, 113 mg). The mixture was hydrogenated overnight, and then filtered through a 0.2 μM membrane. The resulting solution was concentrated in vacuo. The residue was diluted with 1 N aq. NaOH (20 mL) and extracted with DCM (2×100 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford crude, racemic N,N,2,2-tetramethyl-3-pyrrolidinamine (0.2930 g, 85% yield) as a pale yellow oil. LCMS: (M+H)+: 143.1.

Workup

  1. filtrationfiltered through a 0.2 μM membrane
  2. concentrationThe resulting solution was concentrated in vacuo
  3. additionThe residue was diluted with 1 N aq. NaOH (20 mL)
  4. extractionextracted with DCM (2×100 mL)
  5. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48b6d3ea945f4be7b6f68792b398124e
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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