Cyanogen Bromide → HCID 59173206, compound

HRID 885184Notes

Reaction equation

HRID 885184 reaction equation
[NH2:1][CH:2]([CH2:5][C:6]([CH3:15])([CH3:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][OH:4].C([O-])([O-])=O.[K+].[K+].Br[C:23]#[N:24]>C1COCC1.CCOC(C)=O>[CH3:14][C:6]([CH3:15])([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:5][CH:2]1[CH2:3][O:4][C:23]([NH2:24])=[N:1]1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 67178702HCID 67178702, compound

Product 1

HCID 59173206HCID 59173206, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (RS)-2-amino-4,4-dimethyl-5-phenyl-pentan-1-ol (0.97 g) at r.t. in THF (15 ml) under an argon atmosphere were added K2CO3 (0.78 g) and a solution of BrCN (0.59 g) in THF (10 ml). The mixture was stirred for 17 h. The suspension was diluted with EtOAc and washed with H2O. The aqueous phase was back-extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4), filtered and concentrated. The crude product was purified by chromatography on Isolute® Flash-NH2 silica gel from Separtis (gradient: cyclohexane→CH2Cl2→CH2Cl2/MeOH 9:1) to give (RS)-4-(2,2-dimethyl-3-phenyl-propyl)-4,5-dihydro-oxazol-2-ylamine (0.59 g) as an off-white sticky solid. MS (ISP): 233.2 ([M+H]+))

Workup

  1. washwashed with H2O
  2. extractionThe aqueous phase was back-extracted with EtOAc
  3. washThe combined organics were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography on Isolute® Flash-NH2 silica gel from Separtis (gradient: cyclohexane→CH2Cl2→CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-dfc9d005d7c24c5ba74f2de6c15e5e0b
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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