2,2,2-trifluoro-N-(7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-propyl-acetamide → 7-Propylamino-5,6,7,8-tetrahydro-naphthalen-2-ol

HRID 983479Notes

Reaction equation

HRID 983479 reaction equation
FC(F)(F)C([N:5]([CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([OH:19])=[CH:14][CH:15]=2)[CH2:10]1)[CH2:6][CH2:7][CH3:8])=O>CO.[OH-].[Na+]>[CH2:6]([NH:5][CH:9]1[CH2:10][C:11]2[CH:12]=[C:13]([OH:19])[CH:14]=[CH:15][C:16]=2[CH2:17][CH2:18]1)[CH2:7][CH3:8]

Participants

4

Reactant 1

HCID 225606602,2,2-trifluoro-N-(7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-propyl-acetamide

Product 1

HCID 100587877-Propylamino-5,6,7,8-tetrahydro-naphthalen-2-olYield 113.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2,2,2-trifluoro-N-(7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-propyl-acetamide (340 mg, 1.03 mmol) in methanol (30 mL) and 1N NaOH (30 mL) were stirred at room temperature for 30 h. The reaction was concentrated and the residue partitioned between EtOAc (40 mL) and water (40 mL). The aqueous layer was extracted twice more with EtOAc (2×30 mL). The combined organic layers were washed with brine (30 mL), dried (MgSO4), and concentrated to afford 7-propylamino-5,6,7,8-tetrahydro-naphthalen-2-ol (240 mg).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue partitioned between EtOAc (40 mL) and water (40 mL)
  3. extractionThe aqueous layer was extracted twice more with EtOAc (2×30 mL)
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cc448f6d45634e529d78d9760c341d4f
Source dataset
uspto-grants-2005_03
Patent number
US06864266B2

Reaction notes

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