Ammonia → HCID 76831091, compound

HRID 1186166Notes

Reaction equation

HRID 1186166 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:15])=[C:6]([C:8]23[CH2:13][CH:12]2[CH2:11][O:10][C:9]3=[O:14])[CH:7]=1.[NH3:16]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:15])=[C:6]([C:8]2([C:9]([NH2:16])=[O:14])[CH2:13][CH:12]2[CH2:11][OH:10])[CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 76831278HCID 76831278, compound

Product 1

HCID 76831091HCID 76831091, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
23 °C

Procedure

To a suspension of (1SR,5RS)-1-(5-bromo-2-fluoro-phenyl)-3-oxa-bicyclo[3.1.0]hexan-2-one (intermediate B5A) (4.6 g, 17 mmol) in dioxane (20 ml) at 23° C. was added ammonia (7 M in MeOH, 40 ml) and the mixture was stirred at 23° C. for 2 days (not complete). Evaporated all volatiles and directly subjected to silica gel chromatography with n-heptane/ethyl acetate to give recovered starting material (0.98 g, 21%) and the title compound as a white solid (3.5 g, 72%). MS (ISP): m/z=287.9 [(M+H)+] and 290.0 [(M+2+H)+].

Workup

  1. customEvaporated all volatiles
  2. customto give
  3. customrecovered

Sources & evidence

ORD record
ord-58cf919906ca47bcb228ee38df822930
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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