Water → (S)-4-[2-(2-Chloro-phenyl)-ethyl]-4-methyl-4,5-dihydro-oxazol-2-ylamine

HRID 1911553Notes

Reaction equation

HRID 1911553 reaction equation
[NH2:1][C@@:2]([CH3:14])([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])[CH2:3][OH:4].C([O-])([O-])=O.[K+].[K+].[N:21]#[C:22]Br.O>C1COCC1.C(OCC)(=O)C>[Cl:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][CH2:5][C@@:2]1([CH3:14])[CH2:3][O:4][C:22]([NH2:21])=[N:1]1

Participants

7

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 68712118(S)-2-Amino-4-(2-chloro-phenyl)-2-methyl-butan-1-ol

Product 1

HCID 24963280(S)-4-[2-(2-Chloro-phenyl)-ethyl]-4-methyl-4,5-dihydro-oxazol-2-ylamineYield 33%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of (S)-2-amino-4-(2-chloro-phenyl)-2-methyl-butan-1-ol (0.190 g, 0.89 mmol) and K2CO3 (0.155 g, 1.12 mmol) in THF (10 ml) under an argon atmosphere was added a solution of cyanogen bromide (0.119 g, 1.12 mmol) in THF (1 ml). The mixture was stirred for 18 hours, then water and ethyl acetate were added. The organic layer was washed with water, dried over MgSO4 and evaporated over Isolute® Flash-NH2 silica gel. Chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/MeOH=90:10) yielded the title compound as off-white solid, (0.070 g, 33%); MS (ISP): 239.2; 241.2 ((M+H)+.).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. customevaporated over Isolute® Flash-NH2 silica gel

Sources & evidence

ORD record
ord-bbfcad8f3d8e42429be36e7f4a417e92
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

Loading…