Sodium Hydroxide → HCID 22596837, compound

HRID 1760833Notes

Reaction equation

[CH3:1][C:2]1([CH3:22])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH:14][C:15](=O)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:5]=[CH:4][C:3]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C(OCC)C.O>[CH2:15]([NH:14][C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:22])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=2[CH:7]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of hexanoic acid (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amide (740 mg, 2.46 mmole) in 20 mL diethyl ether (ether) was treated with 400 mg of lithium aluminium hydride (LAH) and the mixture was heated to reflux for 90 minutes. After cooling to 0° C., 0.4 mL of water, 0.4 mL of 15% aqueous sodium hydroxide solution and 1.2 mL of water were successively added and the reaction mixture was stirred at room temperature for 30 minutes. MgSO4 was added and the mixture was filtered and concentrated in vacuo to provide a pale yellow oil. The product was purified by flash chromatography SiO2, 5% ethyl acetate/hexanes) to yield 635 mg (81%) of hexyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (17) as a colorless oil.

Workup

temperaturethe mixture was heated
temperatureto reflux for 90 minutes
filtrationthe mixture was filtered
concentrationconcentrated in vacuo
customto provide a pale yellow oil
customThe product was purified by flash chromatography SiO2, 5% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-e8880323cd7245f48fcd28430c2da29f
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06844466B2

Reaction notes

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