Hydrochloric Acid → HCID 86707704, compound

HRID 1408948Notes

Reaction equation

HRID 1408948 reaction equation
C([NH:8][CH:9]1[CH2:13][CH2:12][C:11]([CH3:15])([OH:14])[C:10]1([F:17])[CH3:16])C1C=CC=CC=1.Cl>[Pd].CO>[NH2:8][C@@H:9]1[CH2:13][CH2:12][C@@:11]([CH3:15])([OH:14])[C@@:10]1([F:17])[CH3:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68291739HCID 68291739, compound

Product 1

HCID 86707704HCID 86707704, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(benzylamino)-2-fluoro-1,2-dimethylcyclopentanol (415 mg, 1.749 mmol, from Step 3), 10% palladium on carbon (93 mg) in methanol (10 mL) and 4 N aqueous hydrochloric acid (0.481 mL, 1.924 mmol) was stirred under hydrogen at 34 psi for 15 h. After removal of catalyst by filtration, the filtrate was concentrated to give (1R,2R,3R)-3-amino-2-fluoro-1,2-dimethylcyclopentanol (racemic mixture) as a hydrochloride salt. 1H NMR (400 MHz, methanol-d4) δ ppm 3.51-3.85 (1 H, m), 2.21-2.55 (1 H, m), 1.95-2.15 (1 H, m), 1.59-1.83 (2 H, m), 1.13-1.57 (6H, m).

Workup

  1. customAfter removal of catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7547c3585449477f8bfec669be1e28b7
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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