Acetic Acid → (RS)-2-(N-ethyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-6-yl)-heptanol

HRID 394944Notes

Reaction equation

HRID 394944 reaction equation
[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:13][OH:14])[CH:10]=2)[NH:5][CH2:4][CH2:3]1.[CH:21](=O)[CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[CH2:21]([N:5]1[C:6]2[C:11](=[CH:10][C:9]([CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:13][OH:14])=[CH:8][CH:7]=2)[C:2]([CH3:20])([CH3:1])[CH2:3][CH2:4]1)[CH3:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 18177893(RS)-2-(4,4-dimethyl-1,2,3,4-tetrahydroquinolin-6-yl)-heptanol

Product 1

HCID 17949416(RS)-2-(N-ethyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-6-yl)-heptanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.5 g of (RS)-2-(4,4-dimethyl-1,2,3,4-tetrahydroquinolin-6-yl)-heptanol, dissolved in 25 ml of methylene chloride, were treated at 0° C. with 0.46 ml of acetaldehyde and 3.46 g of sodium triacetoxyborohydride, then 0.62 ml of acetic acid was added. The mixture was stirred at room temperature for 18 hours. The reaction mixture was quenched with the addition of one portion of 25 ml of water and then, was extracted with two portions of 25 ml of methylene chloride. The combined organic phases were dried over MgSO4 and concentrated in vacuo. The product was purified by flash chromatography (SiO2, 25% ethyl acetate/hexanes). 1H NMR (CDCl3): 6.98 (d, J=2.2 Hz, 1H), 6.85 (dd, J=8.4, 2.2 Hz, 1H), 6.56 (d, J=8.4 Hz, 1H), 3.75-3.55 (m, 2H), 3.33 (q, J=7.1 Hz, 2H), 3.30-3.20 (m, 2H), 2.70-2.55 (m, 1H), 1.80-1.70 (m, 2H), 1.70-1.45 (m, 2H), 1.45-1.20 (m, 6H), 1.26 (s, 6H), 1.14 (t, J=7.1 Hz, 3H), 0.84 (t, J=6.5 Hz, 3H).

Workup

  1. customThe reaction mixture was quenched with the addition of one portion of 25 ml of water
  2. extractionwas extracted with two portions of 25 ml of methylene chloride
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash chromatography (SiO2, 25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-e74b9f42147b47b1923c9725900478e8
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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