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

HRID 750394Notes

Reaction equation

HRID 750394 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.[ClH:16]>C(O)C.[Pd]>[ClH:16].[CH3:13][C:11]1([CH3:14])[CH2:12][NH:8][CH2:9][C@H:10]1[OH:15]

Participants

5

Reactant 2

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

Product 1

HCID 66936381(S)-4,4-Dimethylpyrrolidin-3-OL hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 702EthanolSolvent

Procedure

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 stirred under hydrogen (40 psi) for 18 h in the presence of 300 mg of 10% Pd/C, after which the amount of 10% Pd/C was doubled and 2 mL of concentrated hydrochloric acid were added. The mixture was stirred for an additional 72 h under hydrogen (40 psi), before the 10% Pd/C was filtered off over celite. The filtrate was concentrated and several portions of toluene were distilled from the residue, which was then dried under high vacuum to afford 4.74 g (quantitative yield) of (3S)-4,4-dimethyl-3-pyrrolidinol hydrochloride. 1H NMR (300 MHz, DMSO-d6) δ 9.46 (m, 2H), 5.43 (br s, 1H), 3.75 (m, 1H), 3.36 (m, 1H), 2.88 (m, 3H), 0.98 (s, 3H), 0.94 (s, 3H).

Workup

  1. filtrationwas 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-f9845205fee549d8a3c916730086ad23
Source dataset
uspto-grants-2008_07
Patent number
US07402606B2

Reaction notes

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