Methanol → (2S)-5-(1,3,5-Trimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 420782Notes

Reaction equation

HRID 420782 reaction equation
C([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[C:19]2[C:20]([CH3:26])=[N:21][N:22]([CH3:25])[C:23]=2[CH3:24])[CH2:10]1)C1C=CC=CC=1.CO>C1COCC1.[Pd]>[CH3:25][N:22]1[C:23]([CH3:24])=[C:19]([C:15]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:16]=2[CH2:17][CH2:18][C@H:9]([NH2:8])[CH2:10]3)[C:20]([CH3:26])=[N:21]1

Participants

5

Reactant 2

HCID 887MethanolHCID 24989524(2S)-Benzyl-[5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amine

Product 1

HCID 24989528(2S)-5-(1,3,5-Trimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydronaphthalen-2-amineYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2S)-benzyl-[5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amine (0.287 g, 0.832 mmol) in THF (4 mL) was added to Pd/C (0.10 g, 10% weight of Pd on activated carbon), and MeOH (10 mL) was added to the suspension. The reaction mixture was stirred under H2 (g) atmosphere (balloon) for 21 h. It was filtered through Celite washing with AcOEt (2×10 mL), the solvent was concentrated off and the crude was purified by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH 95:5:1), to yield 0.178 g of the title product (Rf=0.2 (AcOEt/MeOH/Et3N 20:3:2), pale yellow colored oil, 84% yield).

Workup

  1. additionwas added to the suspension
  2. filtrationIt was filtered through Celite
  3. washwashing with AcOEt (2×10 mL)
  4. concentrationthe solvent was concentrated off
  5. customthe crude was purified by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH 95:5:1)

Sources & evidence

ORD record
ord-732ef19a7fdc4ee89865cad25bc01e51
Source dataset
uspto-grants-2012_01
Patent number
US08097641B2

Reaction notes

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