Acetic Acid → HCID 86755984, compound

HRID 370042Notes

Reaction equation

HRID 370042 reaction equation
[CH3:1][O:2][C:3](=[O:35])[N:4]([CH2:20][C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][C@@H:7]([CH3:19])[CH2:6]1.C(O)(=O)C.[CH:40](=O)[CH2:41][CH2:42][CH3:43].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClC(Cl)C.O>[CH3:1][O:2][C:3](=[O:35])[N:4]([CH2:20][C:21]1[CH:26]=[C:25]([C:27]([F:28])([F:30])[F:29])[CH:24]=[C:23]([C:31]([F:33])([F:32])[F:34])[CH:22]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([CH2:40][CH2:41][CH2:42][CH3:43])[C@@H:7]([CH3:19])[CH2:6]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 261ButanalHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86755985HCID 86755985, compound

Product 1

HCID 86755984HCID 86755984, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A solution of cis-(3,5-bis-trifluoromethyl-benzyl)-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid methyl ester (Example 67) (34 mg, 0.067 mmol), acetic acid (4 μL, 0.067 mmol), butyraldehyde (17 μL, 0.34 mmol), and sodium triacetoxyborohydride (71 μL, 0.34 mmol) in anhydrous dichloroethane (1 mL) were stirred at room temperature overnight. Water (5 mL) was added, the aqueous phase made basic with potassium carbonate, and the mixture was extracted with ethyl acetate (3×10 mL). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel chromatography using 0-15% ethyl acetate/hexanes as eluent afforded 32 mg of the title compound (82%):MS m/z 563 (M+ +1); 1H NMR (CDCl3) δ 6.31 (C8, s, 1H), 3.64 (CO2Me, s, 3H), 1.20 (C2-Me, d, 3H, J=6.3 Hz). The hydrochloride salt was prepared by treating an ethereal solution of the free base with an ethereal solution of HCl. Hydrochloride salt:1H NMR (CDCl3) δ 3.83 (CO2Me, s, 3H), 1.20 (C2-Me, d, 3H, J=6.4 Hz).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×10 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-e0e4d9444a984ab19fbaa6a60c2627a8
Source dataset
uspto-grants-2000_10
Patent number
US06140342

Reaction notes

Loading…