Cyanogen Bromide → (S)-4-((S)-2-Phenylbutyl)-4,5-dihydrooxazol-2-amine

HRID 2276363Notes

Reaction equation

HRID 2276363 reaction equation
[NH2:1][C@@H:2]([CH2:5][C@@H:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:7][CH3:8])[CH2:3][OH:4].C([O-])(=O)C.[Na+].[N:20]#[C:21]Br>CO>[C:9]1([C@@H:6]([CH2:7][CH3:8])[CH2:5][C@H:2]2[CH2:3][O:4][C:21]([NH2:20])=[N:1]2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 66705857(2S,4S)-2-amino-4-phenylhexan-1-ol

Product 1

HCID 24963286(S)-4-((S)-2-Phenylbutyl)-4,5-dihydrooxazol-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred, cooled (0° C.) solution of (2S,4S)-2-amino-4-phenyl-hexan-1-ol (270 mg, 1.40 mmol) and sodium acetate (229 mg, 2.70 mmol) in methanol (20 ml) was added dropwise a solution of cyanogen bromide (180 mg, 1.68 mmol) in methanol (2 ml) over 10 min. The mixture was then allowed to warm to r.t. and stirring was continued for 16 h. The mixture was concentrated in vacuo and the residue was taken up in ethyl acetate and washed sequentially with saturated aqueous sodium bicarbonate solution and with saturated brine. The organic phase was dried over sodium sulphate and concentrated in vacuo. The residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: heptane/EtOAc/MeOH) to yield a light yellow solid. MS (ISP): 219.3 ([M+H]+).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washwashed sequentially with saturated aqueous sodium bicarbonate solution and with saturated brine
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: heptane/EtOAc/MeOH)
  6. customto yield a light yellow solid

Sources & evidence

ORD record
ord-dd6ab984a291489dae041aa350885075
Source dataset
uspto-grants-2015_09
Patent number
US09132136B2

Reaction notes

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