Triethylsilane → HCID 86685936, compound

HRID 2277609Notes

Reaction equation

HRID 2277609 reaction equation
C([SiH](CC)CC)C.[CH2:8]([C:15]1(O)[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([Cl:24])[CH:22]=2)[C:17](=[O:25])[NH:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(C1(O)C2C(=CC(Cl)=CC=2)C(=O)N1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[CH2:8]([CH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([Cl:24])[CH:22]=2)[C:17](=[O:25])[NH:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 86685937HCID 86685937, compoundHCID 86685938HCID 86685938, compound

Product 1

HCID 86685936HCID 86685936, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Under N2 protection, triethylsilane (23 g, 200 mmol) and TFA (10 mL) were added successively to a mixture of 3-benzyl-5-chloro-3-hydroxy-2,3-dihydro-isoindol-1-one and 3-benzyl-6-chloro-3-hydroxy-2,3-dihydro-isoindol-1-one (5.47 g, 20 mmol). After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The residue was treated with a satd. aq. NaHCO3 solution (30 mL) and extracted with DCM (2×30 mL). The combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude mixture of products. The desired regioisomer, 3-benzyl-5-chloro-2,3-dihydro-isoindol-1-one was obtained by prep-HPLC separation as a white solid (1.03 g, 20%). MS: 258.1 (M+H+).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was treated with a satd
  3. extractionaq. NaHCO3 solution (30 mL) and extracted with DCM (2×30 mL)
  4. washThe combined organic layers were washed with brine
  5. customdried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo
  8. customto give a crude
  9. additionmixture of products

Sources & evidence

ORD record
ord-c11f872d985e4193b3fb36b40382ede3
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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