Borane → 1,1-Dimethylethyl 4-{[3'-(aminomethyl)-3-biphenylyl]methyl}-1-piperazinecarboxylate

HRID 2080314Notes

Reaction equation

HRID 2080314 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].B>C1COCC1>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]3[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH2:21]3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 577366971,1-Dimethylethyl 4-[(3'-cyano-3-biphenylyl)methyl]-1-piperazinecarboxylate

Product 1

HCID 577367131,1-Dimethylethyl 4-{[3'-(aminomethyl)-3-biphenylyl]methyl}-1-piperazinecarboxylateYield 24.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,1-dimethylethyl 4-[(3′-cyano-3-biphenylyl)methyl]-1-piperazinecarboxylate (4.5 g) in THF (30 mL) was treated with borane. THF (47.7 mL, 1M in THF) and the resulting mixture was heated at reflux for 1 hour. After cooling to room temperature, the reaction mixture was quenched with saturated ammonium chloride solution (20 mL) and extracted with ethyl acetate (3×30 mL). The combined organics were dried (MgSO4), concentrated under vacuum to give a residue which was purified by flash chromatography on silica (100 g) to yield the title compound (1.1 g). LC/MS: m/z, 382 (M+H), 1.86 min.

Workup

  1. temperatureat reflux for 1 hour
  2. customthe reaction mixture was quenched with saturated ammonium chloride solution (20 mL)
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. dry with materialThe combined organics were dried (MgSO4)
  5. concentrationconcentrated under vacuum
  6. customto give a residue which
  7. customwas purified by flash chromatography on silica (100 g)

Sources & evidence

ORD record
ord-5b5c9474880a4d6bb6b1e58ec751756f
Source dataset
uspto-grants-2011_04
Patent number
US07932247B2

Reaction notes

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