Hydrochloric Acid → HCID 86605117, compound

HRID 2118351Notes

Reaction equation

HRID 2118351 reaction equation
B.CSC.B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.[N:26]([CH2:29][C:30]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[C:34]([F:46])[CH:33]=1)=[O:31])=[N+:27]=[N-:28].Cl>C1COCC1.C1(C)C=CC=CC=1>[N:26]([CH2:29][C@@H:30]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[C:34]([F:46])[CH:33]=1)[OH:31])=[N+:27]=[N-:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 12423031(Dimethyl sulfide)trihydroboron2×HCID 85939649HCID 85939649, compound

Product 1

HCID 86605117HCID 86605117, compoundYield 466.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Borane-dimethylsulphide solution in THF (2M, 0.03 mL) was added to a solution of (R)-2-methyl-CBS-oxazaborolidine in toluene (1M, 0.06 mL) at 0° with stirring. The reaction mixture was stirred for 15 min prior to the dropwise addition of a solution of 2-azido-1-[4-(benzyloxy)-3-fluorophenyl]ethanone (100 mg) in THF. Further Borane-dimethylsulphide in THF (2M, 0.03 mL) was added dropwise and the reaction mixture stirred at 0° for 2 h. 2M HCl(aq) (2 mL) was added dropwise and the reaction mixture stirred for 10 min prior to partitioning the reaction mixture between diethyl ether and water. The organic phase was washed twice with 2M HCl(aq), three times with sat. NaHCO3(aq), water and brine. The organic phase was dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with DCM to give the title compound (470 mg). LCMS RT=3.36 min.

Workup

  1. stirringThe reaction mixture was stirred for 15 min
  2. stirringthe reaction mixture stirred at 0° for 2 h
  3. stirringthe reaction mixture stirred for 10 min
  4. customto partitioning the reaction mixture between diethyl ether and water
  5. washThe organic phase was washed twice with 2M HCl(aq), three times with sat. NaHCO3(aq), water and brine
  6. customThe organic phase was dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluting with DCM

Sources & evidence

ORD record
ord-ca7c347000a24688ac55ac4fa2f1b73b
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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