HCID 68863067, compound → 2-Amino-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid

HRID 1725902Notes

Reaction equation

HRID 1725902 reaction equation
C(OC([NH:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[C:19]([OH:21])=[O:20])=O)(C)(C)C>C(O)(=O)C>[NH2:8][C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]=1[C:19]([OH:21])=[O:20]

Participants

3

Reactant 1

HCID 68863067HCID 68863067, compound

Product 1

HCID 688630822-Amino-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acidYield 86.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of Example 128B (14.21 g, 49.46 mmol) and Pt2O (7.00 g, 30.8 mmol) in acetic acid (200 mL) was shaken in a reactor pressurized with 60 psi of H2 at 25° C. for 80 hours, filtered, and concentrated. The concentrate was treated with dichloromethane (142 mL) and TFA (24 mL) and stirred for 3 hours. The organic layer was washed with NaOH (2×250 mL) and brine (200 mL), dried (MgSO4), filtered, and concentrated to provide the desired product (8.17 g, 86%). MS (ESI(+)) m/e 192 (M+H)+; MS (ESI(−)) m/e 190 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 6.83 (d, 1H), 6.53 (d, 1H), 2.72 (m, 2H), 2.57 (m, 2H), 1.64 (m, 4H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionThe concentrate was treated with dichloromethane (142 mL) and TFA (24 mL)
  4. washThe organic layer was washed with NaOH (2×250 mL) and brine (200 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-42f31aba43374a05880b4396f9289177
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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