Hydrochloric Acid → (S)-4,4-Dimethylpyrrolidin-3-OL hydrochloride

HRID 1182298Notes

Reaction equation

HRID 1182298 reaction equation
C([N:8]1[CH2:12][C:11]([CH3:14])([CH3:13])[C@H:10]([OH:15])[CH2:9]1)C1C=CC=CC=1.[H][H].[ClH:18]>C(O)C.[Pd]>[ClH:18].[CH3:13][C:11]1([CH3:14])[CH2:12][NH:8][CH2:9][C@H:10]1[OH:15]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 10442950(3S)-1-benzyl-4,4-dimethyl-3-pyrrolidinolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 66936381(S)-4,4-Dimethylpyrrolidin-3-OL hydrochlorideYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

To a solution of 6.34 g (41.7 mmol) of (3S)-1-benzyl-4,4-dimethyl-3-pyrrolidinol in 250 mL of ethanol and 50 mL of 1N hydrochloric acid was added 300 mg of 10% palladium on carbon. The reaction mixture was stirred under 40 psi of hydrogen gas for 18 h. To the reaction mixture was added 300 mg of 10% palladium on carbon and 2 mL of concentrated hydrochloric acid. The reaction mixture was stirred under 40 psi of hydrogen gas for 72 h. The catalyst was filtered off over celite, and the filtrate was concentrated. Several portions of toluene were distilled from the residue, which was then dried under high vacuum to afford 4.74 g (>99%) of (3S)-4,4-dimethyl-3-pyrrolidinol hydrochloride. 1H-NMR (300 MHz, DMSO-d6): δ 9.46 (d, J=40 Hz, 2H), 5.43 (br s, 1H), 3.75 (m, 1H), 3.36 (m, 1H), 2.88 (m, 3H), 0.96 (d, J=10 Hz, 6H).

Workup

  1. filtrationThe catalyst was filtered off over celite
  2. concentrationthe filtrate was concentrated
  3. distillationSeveral portions of toluene were distilled from the residue, which
  4. customwas then dried under high vacuum

Sources & evidence

ORD record
ord-03c200861809417daffbeb11829b1758
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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