Benzaldehyde → HCID 11117199, compound

HRID 459917Notes

Reaction equation

HRID 459917 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH4-].[Na+]>CO>[CH2:9]([NH:1][CH:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 178511715HCID 178511715, compound

Product 1

HCID 11117199HCID 11117199, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Combine trans-4-amino-cyclohexanol (2.0 g, 17.4 mmol) in methanol (75 mL) in a sealed tube then add benzaldehyde (1.85 mL, 18.23 mmol). Heat the reaction mixture at 70° C. while stirring for 2 h. Then let the reaction cool down and add sodium borohydride (2.46 g, 65.1 mmol) in portions. Stir overnight. Evaporate the solvent till ⅓ of the original volume. Partition the reaction mixture between EtOAc (50 mL) and water (40 mL). Reextract the aqueous layer with EtOAc (20 mL). Combine the organic layers and dry over sodium sulfate. Filter and concentrate to provide the title compound (3.5 g) that will be use directly in the next step.

Workup

  1. temperaturecool down and
  2. stirringStir overnight
  3. customEvaporate the solvent till ⅓ of the original volume
  4. customPartition the reaction mixture between EtOAc (50 mL) and water (40 mL)
  5. dry with materialCombine the organic layers and dry over sodium sulfate
  6. filtrationFilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-3bcc0ed927f4456ba2f767636ba5f884
Source dataset
uspto-grants-2007_03
Patent number
US07196100B2

Reaction notes

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