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

HRID 238752Notes

Reaction equation

HRID 238752 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 SaltYield 109.2%

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 Pd(OH)2/C (20% wt, 627 mg). The reaction mixture was degassed with Ar and stirred at rt under H2 atmosphere for 3 days. The resulting solid was filtered and rinsed with EtOH. The filtrate was concentrated to yield (1R,2R)-2-aminocyclopentanol TFA salt (4.3 g, 100% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-D6) ppm 1.00-1.13 (m, 1H), 1.39-1.57 (m, 2H), 1.56-1.76 (m, 2H), 1.79-1.94 (m, 1H), 1.94-2.10 (m, 1H), 3.06-3.23 (m, 1H), 3.88-4.02 (m, 1H), 7.84-8.07 (m, 2H).

Workup

  1. customThe reaction mixture was degassed with Ar
  2. filtrationThe resulting solid was filtered
  3. washrinsed with EtOH
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ac2760ab66e8457b8964b4cfdcabff12
Source dataset
uspto-grants-2014_02
Patent number
US08642576B2

Reaction notes

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