Acetic Acid → HCID 67467860, compound

HRID 509283

Reaction equation

HRID 509283 reaction equation
[OH:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[CH:10]1([NH2:13])[CH2:12][CH2:11]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C.[OH-].[Na+]>ClCCCl>[CH:10]1([NH:13][CH:5]2[CH2:6][CH2:7][C:2]([CH3:9])([OH:1])[CH2:3][CH2:4]2)[CH2:12][CH2:11]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 285394-Hydroxy-4-methylcyclohexanoneHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67467860HCID 67467860, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-Hydroxy-4-methylcyclohexanone (440 mg, 3.43 mmol) was dissolved in 1,2-dichloroethane (15 ml), followed by sequential addition of cyclopropylamine (0.26 ml, 3.78 mmol), NaBH(OAc)3 (1.16 g, 5.49 mmol), and acetic acid (0.20 ml, 3.43 mmol), and then the resulting mixture was stirred at room temperature under nitrogen stream for 20 hours. The resulting reaction liquid was neutralized by addition of 10% aqueous NaOH solution, and extracted with 5% MeOH/MC (15 ml×4). The organic layer was dried over anhydrous sodium sulfate, followed by filtration, concentration, and vacuum drying, to obtain 417 mg of yellow solid (72%).

Workup

  1. customThe resulting reaction liquid
  2. extractionextracted with 5% MeOH/MC (15 ml×4)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfollowed by filtration, concentration, and vacuum
  5. customdrying

Sources & evidence

ORD record
ord-2220842ccbbd4c5480c96cb0cd86947b
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Linked notes

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