Aniline → HCID 178453937, compound

HRID 2391006Notes

Reaction equation

HRID 2391006 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH:14]=O)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].CCCC(C)C>ClCCl>[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 6115AnilineHCID 78922-MethylpentaneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 178453955HCID 178453955, compound

Product 1

HCID 178453937HCID 178453937, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans-(4-Formyl-cyclohexyl)carbamic acid tert-butyl ester (3.27 g, 14.38 mmol) and aniline (1.98 mL, 15.81 mmol) are dissolved in dichloromethane (60 mL) at room temperature. Sodium triacetoxyborohydride (4.57 g, 21.57 mmol) is added in one portion and the mixture is stirred at room temperature for 2.5 hours. 1N sodium hydroxide solution (20 mL) is added and the mixture is stirred at room temperature for a further 10 minutes. The DCM layer is separated and washed successively with water and saturated brine, dried (MgSO4), filtered and evaporated to give a colourless solid. This is slurried with iso-hexane, filtered and dried to give a colourless solid; [MH+ 305]

Workup

  1. stirringthe mixture is stirred at room temperature for a further 10 minutes
  2. customThe DCM layer is separated
  3. washwashed successively with water and saturated brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a colourless solid
  8. filtrationfiltered
  9. customdried
  10. customto give a colourless solid

Sources & evidence

ORD record
ord-1afc0f155e3d4b5a96eab3b203346af3
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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