Sodium borohydride → HCID 18172455, compound

HRID 397090Notes

Reaction equation

HRID 397090 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][N:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=O)[CH:6]=[CH:7][CH:8]=1.[BH4-].[Na+]>O=P(Cl)(Cl)Cl.C(Cl)Cl>[CH:14]1([CH:12]2[C:6]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH2:9][CH2:10][N:11]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 86583960HCID 86583960, compound

Product 1

HCID 18172455HCID 18172455, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

A stirred solution of cyclohexanecarboxylic acid [2-(3-methoxy-phenyl)-ethyl]-phenyl-amide in POCl3 under an atmosphere of N2 was heated at reflux for 14 hours. The solution was allowed to cool to rt and concentrated in vacuo. The residue was taken up in CH2Cl2 (30 ml) and washed with sat. NaHCO3 until CO2 evolution ceased. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was dissolved in MeOH (20 ml), cooled to 0° C., and NaBH4 (0.105 g, 2.77 mmol) was added in a portionwise manner. The reaction was stirred for 2 hours at 0° C., then additional NaBH4 (0.105 g, 2.77 mmol) was added. The reaction was stirred at rt overnight, diluted with CH2Cl2 (50 ml), and washed with sat. NaHCO3 solution (1×50 ml). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo, to give the desired compound as a yellow oil (0.234 g, 0.729 mmol, 73% yield).

Workup

  1. temperatureat reflux for 14 hours
  2. concentrationconcentrated in vacuo
  3. washwashed with sat. NaHCO3 until CO2 evolution
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in MeOH (20 ml)
  8. temperaturecooled to 0° C.
  9. stirringThe reaction was stirred at rt overnight
  10. washwashed with sat. NaHCO3 solution (1×50 ml)
  11. dry with materialThe organic layer was dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4503f2503bb4581bf8416dd973f269b
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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