Methyl morpholine oxide → (E)-2-Fluoro-3-(6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinolin-8-yl)-but-2-en-1-ol

HRID 1582093Notes

Reaction equation

[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([CH:19]([CH3:21])[CH3:20])=[CH:10][C:11]=2/[C:13](/[CH3:18])=[C:14](/[F:17])\[CH2:15][OH:16])[C:6]([CH3:23])([CH3:22])[CH2:5][CH2:4]1)[CH3:2].[CH3:24][N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:17]/[C:14](=[C:13](/[C:11]1[CH:10]=[C:9]([CH:19]([CH3:20])[CH3:21])[CH:8]=[C:7]2[C:12]=1[N:3]([CH2:1][CH2:2][CH3:24])[CH2:4][CH2:5][C:6]2([CH3:22])[CH3:23])\[CH3:18])/[CH2:15][OH:16]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (E)-3-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-2-fluoro-but-2-en-1-ol (Intermediate 18, 133 mg, 0.35 mmol) in 2 ml of CH2Cl2 at 0° C. was added 4-methylmorpholine N-oxide (83 mg, 0.71 mmol), tetrapropylammonium perruthenate (18.6 mg, 0.05 mmol), and 4 Å molecular sieve powder (10 mg). The mixture was stirred at 0° C. for 5 min, and the bath was removed. The temperature of reaction mixture was monitored carefully, and as soon as the temperature rose to 25° C., the reaction was re-cooled in an ice bath. The cooled reaction mixture was loaded onto a pre-packed silica gel column, and the product was eluted with 100% hexane followed by 2% ethyl acetate in hexane to yield the title compound as a bright yellow solid.

Workup

customthe bath was removed
customThe temperature of reaction mixture
customrose to 25° C.
temperaturethe reaction was re-cooled in an ice bath
customThe cooled reaction mixture
washthe product was eluted with 100% hexane

Sources & evidence

ORD record: ord-ef33253507bb40b79eac1d72a1961caf
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734193B1

Reaction notes

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