Boron trifluoride etherate → HCID 57518631, compound

HRID 1258121Notes

Reaction equation

HRID 1258121 reaction equation
O[CH:2]1[O:8][CH2:7][C@@:6]2([CH3:12])[C:9]([CH3:11])([CH3:10])[C@:3]1([NH:13][C:14](=[O:16])[CH3:15])[CH2:4][CH2:5]2.[SiH](CC)(CC)CC.B(F)(F)F.CCOCC>ClCCl>[CH3:12][C@:6]12[C:9]([CH3:10])([CH3:11])[C@:3]([NH:13][C:14](=[O:16])[CH3:15])([CH2:4][CH2:5]1)[CH2:2][O:8][CH2:7]2

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 57518630HCID 57518630, compound

Product 1

HCID 57518631HCID 57518631, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of step 2 intermediate (0.2 g, 0.88 mmol) in dry dichloromethane (5 mL) under nitrogen atmosphere, was added Et3SiH (0.84 mL; 5.28 mmol) at 0° C. To this boron trifluoride etherate (0.33 mL, 2.6 mmol) was added dropwise over a period of 10 minutes. Stirring was continued for 5 hours at room temperature. After completion, the reaction mixture was quenched with saturated NaHCO3 solution and extracted with dichloromethane. Organic layer was separated and dried over anhydrous Na2SO4. Dichloromethane layer was concentrated under reduced pressure to obtain 165 mg of title compound. 1H NMR (400 MHz, CDCl3) δ ppm: 0.78 (s, 3H), 0.89 (s, 3H), 1.1 (s, 3H), 1.60-1.64 (m, 1H), 1.72-1.78 (m, 2H), 1.85 (s, 3H), 2.60-2.67 (m, 1H), 3.06 (d, J=10.96 Hz, 1H), 3.67 (d, J=10.92 Hz, 1H), 3.78 (d, J=10.48 Hz, 1H), 3.92 (d, J=10.48 Hz, 1H) 5.16 (bs, 1H). m/z (M+1): 212.2.

Workup

  1. customAfter completion, the reaction mixture was quenched with saturated NaHCO3 solution
  2. extractionextracted with dichloromethane
  3. customOrganic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationDichloromethane layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fb808bf2d129401599cab9070dafff07
Source dataset
uspto-grants-2013_06
Patent number
US08466145B2

Reaction notes

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