Acetic Acid → HCID 178497925, compound

HRID 967638Notes

Reaction equation

HRID 967638 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

1H NMR (CDCl3), 300 MHz; δ 8.36 (s, 1H); 8.07 (d, 2H); 7.81 (d, 2H); 3.92 (s, 3H); 3.54 (m, 1H); 1.55-1.92 (m, 8H); 1.14 (m, 1H); 0.90 (s, 9H). 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 sodium sulphate. 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 sodium sulphate
  5. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-6b6323660a5145698c60fae833d877d9
Source dataset
uspto-grants-2005_10
Patent number
US06953812B2

Reaction notes

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