Trimethylsilyl cyanide → HCID 118062127, compound

HRID 920810Notes

Reaction equation

HRID 920810 reaction equation
[O:1]1[CH2:5][CH2:4][C:3](=[N:6][S:7]([C:9]([CH3:12])([CH3:11])[CH3:10])=[O:8])[CH2:2]1.[Si]([C:17]#[N:18])(C)(C)C>C(Cl)Cl>[C:17]([C:3]1([NH:6][S:7]([C:9]([CH3:12])([CH3:11])[CH3:10])=[O:8])[CH2:4][CH2:5][O:1][CH2:2]1)#[N:18]

Participants

4

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 131734889HCID 131734889, compound

Product 1

HCID 118062127HCID 118062127, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 334A (300 mg, 1.585 mmol) in DCM (10 mL) at RT was added TMSCN (198 μL, 1.477 mmol) dropwise, followed by Ti(OEt)4 (318 μL, 1.426 mmol). The resulting solution was stirred for 12 h. The reaction was quenched by pouring it into a vigorously stirred saturated aq. solution of NaHCO3 (20 mL). The precipitate was filtered off and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude compound was triturated with diethyl ether to afford Intermediate 334B (150 mg, 44% yield) as a pale brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.48-6.36 (m, 1H), 4.05 (d, J=9.0 Hz, 1H), 3.87 (d, J=8.5 Hz, 3H), 2.49-2.33 (m, 2H), 1.21-1.10 (m, 9H).

Workup

  1. customThe reaction was quenched
  2. additionby pouring it into a vigorously stirred saturated aq. solution of NaHCO3 (20 mL)
  3. filtrationThe precipitate was filtered off
  4. extractionthe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude compound was triturated with diethyl ether

Sources & evidence

ORD record
ord-1221fec692674233bcf175fa8c4137d7
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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