Acetic Acid → HCID 70873960, compound

HRID 2208940Notes

Reaction equation

HRID 2208940 reaction equation
[NH2:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[OH:13][C:14]1([CH3:21])[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C>[OH:13][C:14]1([CH3:21])[CH2:19][CH2:18][CH:17]([NH:1][C:2]2[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:16][CH2:15]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 285394-Hydroxy-4-methylcyclohexanoneHCID 516892Sodium BicarbonateHCID 38010253-Amino-2-methylbenzoic acid methyl esterHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 70873960HCID 70873960, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of methyl 3-amino-2-methylbenzoate (1.5 g, 9.1 mmol) and 4-hydroxy-4-methylcyclohexanone (1.51 ml, 11.8 mmol) in 10 ml of dichloroethane was added acetic acid (3.2 mL, 55 mmol) and the reaction mixture stirred at room temperature for 20 minutes. The reaction mixture was cooled to 0° C. and sodium triacetoxyborohydride (5.78 g, 27.3 mmol) was added and the mixture stirred at room temperature overnight. The reaction mixture was neutralized with sat. NaHCO3, extracted with DCM, dried over Na2SO4, concentrated under reduced pressure, and purified by silica gel column chromatography to afford the title compound which was carried forward as a mixture of cis and trans isomers (1.4 g, 56%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringthe mixture stirred at room temperature overnight
  3. extractionextracted with DCM
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-14bccd42127f48589e4463a047a066f9
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

Loading…