HCID 68694352, compound → HCID 68691308, compound

HRID 1175216Notes

Reaction equation

HRID 1175216 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[O:12])[CH:9]=2)[CH2:4][CH2:3]1>C1(C)C=CC=CC=1.C1COCC1>[OH:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[O:12])[CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 68694352HCID 68694352, compound

Product 1

HCID 68691308HCID 68691308, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of R-CBS reagent (90 μL, 1M sol.) and BH3DMS (220 μL, 2.34 mmol) in 3.6 ml of toluene at −10° C. was dropwise added over about 2 h, a solution of the product from Step 1 (500 mg, 1.8 mmol) in 1.8 mL of THF. After addition was complete, the reaction mixture was quenched with 0.5 N HCl. The resulting mixture was transferred to a seperatory funnel and the aqueous layer was washed 3× with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated to yield an oil, which was was purified by chiral HPLC (77% ee prior to chiral separation) to afford the title compound.

Workup

  1. additionAfter addition
  2. customthe reaction mixture was quenched with 0.5 N HCl
  3. customThe resulting mixture was transferred to a seperatory funnel
  4. washthe aqueous layer was washed 3× with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield an oil, which
  9. customwas was purified by chiral HPLC (77% ee
  10. customto chiral separation)

Sources & evidence

ORD record
ord-2ec34932652a457d9175eade0328b733
Source dataset
uspto-grants-2010_11
Patent number
US07838676B2

Reaction notes

Loading…