HCID 89397317, compound → HCID 71244879, compound

HRID 2171597Notes

Reaction equation

HRID 2171597 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:13][CH2:12][N:11](/[N:14]=[CH:15]/[C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([Cl:24])[C:17]=2[CH3:25])[C@@H:10]1[CH:26]=[O:27])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(Cl)Cl.O>[Si:1]([O:8][C@@H:9]1[C@@H:10]2[N:11]([N:14]=[C:15]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([Cl:24])[C:17]=3[CH3:25])[C@H:26]2[OH:27])[CH2:12][CH2:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 89397317HCID 89397317, compound

Product 1

HCID 71244879HCID 71244879, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of intermediate (IIIa) 4-((E)-((2S,3S)-3-(tert-butyldimethylsilyloxy)-2-formylpyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile (7.0 g, 0.0172 moles) in DCM (100 mL) at 0° C. was added borontrifluoride diethyl etherate (6.2 mL, 0.0207 moles) and reaction mixture was stirred at room temperature for 3 h. Once the starting material had disappeared (monitored by TLC), the reaction mixture was diluted with DCM, water and washed with saturated NaHCO3 aqueous solution, water, brine, dried over Na2SO4 and concentrated to get the crude product. Purification of the crude by column chromatography over silica gel using 10% EtOAc in hexane as a solvent provided the title compound.

Workup

  1. washwashed with saturated NaHCO3 aqueous solution, water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto get the crude product
  5. customPurification of the crude by column chromatography over silica gel using 10% EtOAc in hexane as a solvent

Sources & evidence

ORD record
ord-fa48132c215b465288651e41b5e441d4
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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