Toluene → HCID 131481771, compound

HRID 629853Notes

Reaction equation

HRID 629853 reaction equation
C1(C)C=CC=CC=1.[CH3:8][C:9]1([CH3:24])[C:13]([CH3:15])([CH3:14])[O:12][B:11]([C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[CH:18]=O)[O:10]1.[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.[BH4-].[Na+]>CCOCC.C(O)=O>[CH3:8][C:9]1([CH3:24])[C:13]([CH3:15])([CH3:14])[O:12][B:11]([C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[CH2:18][NH:31][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[O:10]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 7965CyclohexylamineHCID 4311764Sodium borohydrideHCID 109773222-Formylphenylboronic acid pinacol ester

Product 1

HCID 131481771HCID 131481771, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

Toluene (250 mL) was added to 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (5.0 g, 21.54 mmol) followed by cyclohexylamine (2.37 g, 23.89 mmol) and formic acid (˜1.0 mL of 88%) to form a clear solution. The mixture was allowed to reflux using a Dean-Stark trap and the toluene/water mixture collected till clear. Upon completion, the mixture was cooled to room temperature and the solution evaporated to 100 mL. MeOH (200 mL) was then added to the reaction mixture followed by NaBH4 (1.63 g, 43.08 mmol) portion wise. The mixture was stirred for 20 min and quenched with water (5 mL). The solution was evaporated to 100 mL and EtOAc (50 mL) was added. The solution was dried with Na2SO4 and the solvent removed by reduced pressure, yielding a white solid. Et2O (200 mL) was then added dissolving half of the white solid. The remaining solid was collected and dried under reduced pressure offering compound 7. Yield: 6.3 g, 46.4%. 1H NMR (CD2Cl2): δ 7.52-7.50 (d, 1H), 7.28-7.27 (m, 2H), 7.15-7.13 (d, 1H), 4.02 (s, 2H), 3.42 (s, 1H), 3.15-3.07 (m, 1H), 1.74-1.61 (m, 5H), 1.29 (s, 12H), 1.19-1.05 (m, 6H).

Workup

  1. customto form a clear solution
  2. temperatureto reflux
  3. customthe toluene/water mixture collected till clear
  4. customthe solution evaporated to 100 mL
  5. additionMeOH (200 mL) was then added to the reaction mixture
  6. customquenched with water (5 mL)
  7. customThe solution was evaporated to 100 mL and EtOAc (50 mL)
  8. additionwas added
  9. dry with materialThe solution was dried with Na2SO4
  10. customthe solvent removed by reduced pressure
  11. customyielding a white solid
  12. dissolutiondissolving half of the white solid
  13. customThe remaining solid was collected
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-b0a182f13bcb48c790829d8ca521a91d
Source dataset
uspto-grants-2016_04
Patent number
US09315526B2

Reaction notes

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