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

HRID 394944ノート

反応式

HRID 394944 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e74b9f42147b47b1923c9725900478e8
出典データセット
uspto-grants-2003_08
特許番号
US06603012B2

反応ノート

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