Acetic Acid → HCID 22640694, compound

HRID 2415204Notes

Reaction equation

HRID 2415204 reaction equation
[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][C:8]([CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:13][OH:14])=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.C=O.[C:23](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(#N)C.O>[CH3:23][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:13][OH:14])[CH:7]=2)[C:2]([CH3:20])([CH3:1])[CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22640679HCID 22640679, compound

Product 1

HCID 22640694HCID 22640694, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-heptan-1-ol (from Example 5.5, step 6) (2.52 g, 9.15 mmole) in 35 mL of acetonitrile was cooled to 0° C. and treated with 6.68 mL of a 37% formaldehyde solution, 5.82 g of sodium triacetoxyborohydride and 2.36 mL of acetic acid. The reaction mixture was stirred at 0° C. for 30 minutes then at room temperature for four hours, diluted with 50 mL of water and extracted with two 50 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes) to yield 2.39 g of 2-(1,4,4-trimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-heptan-1-ol as a pale yellow oil.

Workup

  1. waitat room temperature for four hours
  2. extractionextracted with two 50 mL portions of ethyl acetate
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil
  7. customThe product was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a8d7430de9c345c98e9516b445cd09d1
Source dataset
uspto-grants-2004_11
Patent number
US06818652B2

Reaction notes

Loading…