Water → HCID 45101107, compound

HRID 2276380Notes

Reaction equation

HRID 2276380 reaction equation
[NH2:1][C@@H:2]([CH2:5][O:6][C@H:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[CH3:8])[CH2:3][OH:4].C([O-])([O-])=O.[K+].[K+].[N:22]#[C:23]Br.O>C1COCC1>[F:15][C:12]1[CH:11]=[CH:10][C:9]([C@@H:7]([O:6][CH2:5][C@H:2]2[CH2:3][O:4][C:23]([NH2:22])=[N:1]2)[CH3:8])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 66705889HCID 66705889, compound

Product 1

HCID 45101107HCID 45101107, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (R)-2-amino-3-[(S)-1-(4-fluoro-phenyl)-ethoxy]-propan-1-ol (1.40 g) in THF (80 ml) were added sequentially K2CO3 (1.82 g) and cyanogen bromide (0.83 g). The mixture was stirred at room temperature for 18 hours, then water was added. The mixture was extracted twice with ethyl acetate and the combined organic layers were dried over MgSO4 and evaporated over Isolute® Flash-NH2 silica gel. Chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: heptane/ethyl acetate=25:75) yielded the title compound as a white solid, (1.15 g, 73%). MS (ISP): 239.0 ([M+H]+).

Workup

  1. extractionThe mixture was extracted twice with ethyl acetate
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. customevaporated over Isolute® Flash-NH2 silica gel

Sources & evidence

ORD record
ord-080f264a5ac745aab880b642f89b6ec1
Source dataset
uspto-grants-2015_09
Patent number
US09132136B2

Reaction notes

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