4-(Bromoacetyl)benzonitrile → HCID 54549064, compound

HRID 2180014Notes

Reaction equation

HRID 2180014 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8]Br)=[CH:5][CH:4]=1)#[N:2].[CH:13]12[CH2:21][CH:17]([CH2:18][NH:19][CH2:20]1)[CH2:16][N:15]([C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH2:14]2.[BH4-].[Na+]>CC#N>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([CH:7]([OH:10])[CH2:8][N:19]2[CH2:20][CH:13]3[CH2:21][CH:17]([CH2:16][N:15]([C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH2:14]3)[CH2:18]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 4311764Sodium borohydrideHCID 53914229HCID 53914229, compound

Product 1

HCID 54549064HCID 54549064, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

4-Cyanophenacyl bromide (225 mg; 1 mmol) was added to a stirred solution of iso-propyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (from step (iv) above; 212 mg; 1 mmol) in MeCN (2 mL). After stirring for 15 min at 0° C., NaBH4 (40 mg; 1 mmol) was added, and the reaction was allowed to warm to rt over 45 minutes. The reaction mixture was concentrated, dissolved in CH2Cl2 and washed with NaHCO3 (aq.) and brine. The organic layer was separated, dried and concentrated to give an oil which was purified using column chromatography (hexane:EtOAc:IPA; 50:49:1) to give the sub-title compound in 35% yield.

Workup

  1. temperatureto warm to rt over 45 minutes
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in CH2Cl2
  4. washwashed with NaHCO3 (aq.) and brine
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated
  8. customto give an oil which
  9. customwas purified

Sources & evidence

ORD record
ord-30dc8061ee13496faa248a3e549ea0b0
Source dataset
uspto-grants-2005_05
Patent number
US06887881B1

Reaction notes

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