Acetic Acid → HCID 178497925, compound

HRID 1633902Notes

Reaction equation

HRID 1633902 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[N:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:14][CH2:13]2)=[CH:6][CH:5]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:14][CH2:13]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 178497924HCID 178497924, compound

Product 1

HCID 178497925HCID 178497925, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

trans-4-[(4-tert-Butylcyclohexylimino)methyl]benzoic acid methyl ester (21.0 g, 69.2 mmol) was suspended in methanol (300 mL), and acetic acid (50 mL) was added. To the resulting clear solution was added sodium cyanoborohydride (3.5 g, 55.5 mmol), and the mixture was stirred at ambient temperature for 30 min. The reaction volume was then reduced to one third by rotary evaporation, and ethyl acetate (500 mL) was added. The organic phase was washed with sodium carbonate solution (5%, 500 mL), and dried with Na2SO4. The solvent was removed by rotary evaporation to leave the title material as a white crystalline solid sufficiently pure for further reactions. Yield: 21.1 g (100%).

Workup

  1. customThe reaction volume was then reduced to one third by rotary evaporation, and ethyl acetate (500 mL)
  2. additionwas added
  3. washThe organic phase was washed with sodium carbonate solution (5%, 500 mL)
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-bfdd6559a5b64fb5bc18677e3f17d0e7
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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