Trifluoroacetic acid → (1R,2R)-2-Amino-cyclopentanol Trifluoroacetic Acid Salt

HRID 1993614Notes

Reaction equation

HRID 1993614 reaction equation
C([O:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[NH2:14])C1C=CC=CC=1.[C:15]([OH:21])([C:17]([F:20])([F:19])[F:18])=[O:16]>CCO.[OH-].[OH-].[Pd+2]>[OH:21][C:15]([C:17]([F:20])([F:19])[F:18])=[O:16].[NH2:14][C@@H:10]1[CH2:11][CH2:12][CH2:13][C@H:9]1[OH:8]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11863649(1R,2R)-trans-2-Benzyloxy-cyclopentylamine

Product 1

HCID 86612967(1R,2R)-2-Amino-cyclopentanol Trifluoroacetic Acid Salt

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of (1R,2R)-2-(benzyloxy)cyclopentanamine (3.5 g, 18.3 mmol) in EtOH (20 mL) was added TFA (1.6 ml, 21.5 mmol), followed by addition of Pd(OH)2/C (20% wt, 627 mg). The reaction mixture was degassed and stirred at ambient temperature under H2 for 3 days, then the solid was removed by filtration and the residue was rinsed with EtOH. The filtrate was concentrated to yield (1R,2R)-2-aminocyclopentanol TFA salt as a yellow oil. (4.3 g, 100%). NMR: 400 MHz 1H (DMSO-D6) 7.96 ppm, 2H, m; 3.95 ppm, 1H, m; 3.17 ppm, 1H, m; 2.02 ppm, 1H, m; 1.87 ppm, 1H, m; 1.66 ppm, 2H, m; 1.48 ppm, 2H, m; 1.07 ppm, 1H, m.

Workup

  1. customThe reaction mixture was degassed
  2. customthe solid was removed by filtration
  3. washthe residue was rinsed with EtOH
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5c2e75750a0846e5b3b5930bb45a5531
Source dataset
uspto-grants-2010_01
Patent number
US07652023B2

Reaction notes

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