Hydrochloric Acid → HCID 76450057, compound

HRID 2276718Notes

Reaction equation

HRID 2276718 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]23[CH:14]([CH:15]=[N:16][O:17][CH3:18])[CH:13]2[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]3)=[CH:5][CH:4]=1.CCCCCC>C(Cl)Cl>[ClH:2].[CH3:18][O:17][N:16]=[CH:15][CH:14]1[C:9]2([C:6]3[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=3)[CH:13]1[CH2:12][NH:11][CH2:10]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 86697410HCID 86697410, compound

Product 2

HCID 313Hydrochloric AcidHCID 76450057HCID 76450057, compoundYield 186.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HCl (g) was bubbled through a solution of tert-butyl 1-(4-chlorophenyl)-6-((methoxyimino)methyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate (210 mg, 0.598 mmol) obtained in step-1 of example 5 in dry DCM (10 mL). After the completion of the reaction as confirmed by TLC, the reaction mixture was purged with excess of nitrogen. The solvent was removed in vacuo to afford a gummy solid which was titurated with hexane to afford hydrochloric acid salt of 1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hexane-6-carbaldehyde O-methyl oxime (140 mg, 81%) as white solid as mixture of isomers.

Workup

  1. customAfter the completion of the reaction
  2. customthe reaction mixture was purged with excess of nitrogen
  3. customThe solvent was removed in vacuo
  4. customto afford a gummy solid which

Sources & evidence

ORD record
ord-33164a0741464b7f95d658ec34d2ce56
Source dataset
uspto-grants-2015_09
Patent number
US09133116B2

Reaction notes

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