Cyanogen Bromide → HCID 58304318, compound

HRID 2424342Notes

Reaction equation

HRID 2424342 reaction equation
[NH2:1][C@@:2]([C:14]1([CH2:17][OH:18])[CH2:16][CH2:15]1)([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[F:13])[CH3:3].[C:19](Br)#[N:20].C([O-])(=O)C.[Na+]>C1COCC1.Cl.O1CCOCC1>[F:13][C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[C@:2]1([CH3:3])[C:14]2([CH2:15][CH2:16]2)[CH2:17][O:18][C:19]([NH2:20])=[N:1]1

Participants

7

Reactant 3

HCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 58304305HCID 58304305, compound

Product 1

HCID 58304318HCID 58304318, compoundYield 54.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Intermediate Ea3 (R1,2=cyclopropyl, R3=Me): To a solution of {1-[(S)-1-amino-1-(2-fluoro-5-nitro-phenyl)-ethyl]-cyclopropyl}-methanol (0.50 g) in dry THF (20 ml) was added bromocyanogen (0.24 g) and sodium acetate (0.19 g) and the mixture was stirred at 80° C. overnight. The mixture was cooled to 22° C., diluted with HCl in dioxane (4M, 2.4 ml) and stirring was continued for 1 h. The mixture was partitioned between aqueous saturated Na2CO3 and ethyl acetate, the organic layer was dried, evaporated and the residue purified by chromatography over silca-NH2 using ethyl acetate to give (S)-8-(2-fluoro-5-nitro-phenyl)-8-methyl-5-oxa-7-aza-spiro[2.5]oct-6-en-6-ylamine (0.30 g) as a pale yellow solid. MS (ESI): m/z=280.1 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to 22° C.
  2. stirringstirring
  3. waitwas continued for 1 h
  4. customThe mixture was partitioned between aqueous saturated Na2CO3 and ethyl acetate
  5. customthe organic layer was dried
  6. customevaporated
  7. customthe residue purified by chromatography over silca-NH2

Sources & evidence

ORD record
ord-f0bb80f88cd4491997039f75547092d7
Source dataset
uspto-grants-2011_06
Patent number
US07964594B1

Reaction notes

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