Acetic Acid → HCID 70874132, compound
Reaction equation
[OH:1][C:2]1([CH3:20])[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[C:10]([CH3:19])=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH2:4][CH2:3]1.[CH:21](=O)[CH3:22].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C>[CH2:21]([N:8]([CH:5]1[CH2:6][CH2:7][C:2]([OH:1])([CH3:20])[CH2:3][CH2:4]1)[C:9]1[C:10]([CH3:19])=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])[CH3:22]Participants
7
Procedure
To a stirred solution of methyl 3-((4-hydroxy-4-methylcyclohexyl)amino)-2-methylbenzoate (1.4 g, 5.05 mmol) and acetaldehyde (0.7 ml, 13 mmol) in 20 ml of dichloroethane was added acetic acid (1.7 mL, 30 mmol) and the reaction mixture was stirred at room temperature for 20 minutes. The reaction mixture was cooled to 0° C. and sodium triacetoxyborohydride (3.2 g, 15 mmol) was added and the mixture was stirred at room temperature for overnight. The reaction mixture was neutralized with sat. NaHCO3 and extracted with DCM. The combined organic layers were dried over Na2SO4, concentrated under reduced pressure, and the residue purified by silica gel column chromatography to afford the title compound (1.42 g, 94%).
Workup
- temperatureThe reaction mixture was cooled to 0° C.
- stirringthe mixture was stirred at room temperature for overnight
- extractionextracted with DCM
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationconcentrated under reduced pressure
- customthe residue purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-96fa7f39e7c140d49807cd38231d96e2
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376422B2
Reaction notes
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