Boron Trichloride → (2S,5R)-6-hydroxy-2-(3-methyl-1,2,4-oxadiazol-5-yl)-1,6-diazabicyclo[3.2.1]octan-7-one

HRID 870864Notes

Reaction equation

HRID 870864 reaction equation
B(Cl)(Cl)Cl.C([O:12][N:13]1[C:19](=[O:20])[N:18]2[CH2:21][C@H:14]1[CH2:15][CH2:16][C@H:17]2[C:22]1[O:26][N:25]=[C:24]([CH3:27])[N:23]=1)C1C=CC=CC=1>C(Cl)Cl>[OH:12][N:13]1[C:19](=[O:20])[N:18]2[CH2:21][C@H:14]1[CH2:15][CH2:16][C@H:17]2[C:22]1[O:26][N:25]=[C:24]([CH3:27])[N:23]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 86701409(2S,5R)-6-(benzyloxy)-2-(3-methyl-1,2,4-oxadiazol-5-yl)-1,6-diazabicyclo[3.2.1]octan-7-one

Product 1

HCID 86701410(2S,5R)-6-hydroxy-2-(3-methyl-1,2,4-oxadiazol-5-yl)-1,6-diazabicyclo[3.2.1]octan-7-oneYield 32.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BCl3 (1M DCM solution, 2.5 mL, 2.5 mmol) was added dropwise to a solution of (2S,5R)-6-(benzyloxy)-2-(3-methyl-1,2,4-oxadiazol-5-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (130 mg, 0.414 mmol) in dry DCM (12 mL) at −78° C. The mixture was stirred at −78° C. to 0° C. for 4 hrs. The reaction mixture was then quenched with MeOH (2 mL). The solvent was removed and the residue was purified by silica gel column chromatography (0 to 10% MeOH/DCM) to afford (2S,5R)-6-hydroxy-2-(3-methyl-1,2,4-oxadiazol-5-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (30 mg, 32%).

Workup

  1. customThe reaction mixture was then quenched with MeOH (2 mL)
  2. customThe solvent was removed
  3. customthe residue was purified by silica gel column chromatography (0 to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-2b1d5dba199249e1bef4bf855c415241
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

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