Water → (S)-4-(2-Phenoxy-ethyl)-4,5-dihydro-oxazol-2-ylamine

HRID 1807886Notes

Reaction equation

HRID 1807886 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH2:6][O: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+].[N:20]#[C:21]Br.O>C1COCC1.C(OCC)(=O)C>[O:7]([CH2:6][CH2:5][C@H:2]1[CH2:3][O:4][C:21]([NH2:20])=[N:1]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 20677773(S)-2-Amino-4-phenoxy-butan-1-ol

Product 1

HCID 59173125(S)-4-(2-Phenoxy-ethyl)-4,5-dihydro-oxazol-2-ylamineYield 31.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of (S)-2-amino-4-phenoxy-butan-1-ol (175 mg) and K2CO3 (200 mg) in THF (5 ml) under an argon atmosphere was added a solution of cyanogen bromide (123 mg) 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=95:5) yielded the title compound as a white solid, (62 mg, 31%); MS (ISP): 207.1 ((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-81a00c7ebb714adc8ca6dcf8fbe46f38
Source dataset
uspto-grants-2013_01
Patent number
US08357712B2

Reaction notes

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