HCID 86584490, compound → (RS)-2-(4,4-dimethyl-1,2,3,4-tetrahydroquinolin-6-yl)-heptanol

HRID 394943Notes

Reaction equation

HRID 394943 reaction equation
[CH3:1][C:2]1([CH3:24])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:13](OCC)=[O:14])[CH:10]=2)[NH:5][C:4](=O)[CH2:3]1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:24])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][OH:14])[CH:10]=2)[NH:5][CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 86584490HCID 86584490, compound

Product 1

HCID 18177893(RS)-2-(4,4-dimethyl-1,2,3,4-tetrahydroquinolin-6-yl)-heptanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

7 g of (RS)-ethyl 2-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-heptanoate were dissolved in 70 ml of toluene and treated, at 0° C., with 4.4 ml of a 10M solution of borane-dimethyl sulfide complex solution in toluene. The mixture was heated to 90° C. for 7 hours. After cooling to room temperature, the mixture was quenched by slow addition of 50 ml of 10% aqueous sodium carbonate solution. The mixture was stirred at room temperature for 30 min. and the phases were separated. The aqueous phase was extracted with two portion of 50 ml of ethyl acetate. The combined extracts were dried over MgSO4 and concentrated in vacuo. The product was purified by flash chromatography (SiO2, 25% ethyl acetate/hexanes). 1H NMR (CDCl3): 6.97 (d, J=2.0 Hz, 1H), 6.76 (dd, J=8.2, 2.0 Hz, 1H), 6.41 (d, J=8.2 Hz, 1H), 3.65 (dd, J=10.6, 5.9 Hz, 1H), 3.57 (dd, J=10.6, 7.9 Hz, 1H), 3.30-3.20 (m, 2H), 2.65-2.55 (m, 1H), 1.80-1.70 (m, 2H), 1.65-1.40 (m, 2H), 1.30-1.15 (m, 6H), 1.27 (s, 6H), 0.86 (t, J=6.6 Hz, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was quenched by slow addition of 50 ml of 10% aqueous sodium carbonate solution
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with two portion of 50 ml of ethyl acetate
  5. dry with materialThe combined extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography (SiO2, 25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2ea2ddacecf74102a18d2b81ebc9e4d8
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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