Boron trifluoride etherate → HCID 58801820, compound

HRID 1985148Notes

Reaction equation

HRID 1985148 reaction equation
B(F)(F)F.CCOCC.[CH2:10]([O:12][C:13](=[O:33])[C:14]([OH:32])([CH3:31])[CH:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)O)[CH3:11].C([SiH](CC)CC)C>C(Cl)Cl>[CH2:10]([O:12][C:13](=[O:33])[C:14]([OH:32])([CH3:31])[CH2:15][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:19][CH:18]=1)[CH3:11]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 58801819HCID 58801819, compound

Product 1

HCID 58801820HCID 58801820, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trifluoride etherate was added to a 0° C. solution of 3-(4-Benzyloxy-phenyl)-2,3-dihydroxy-2-methyl-propionic acid ethyl ester (12.9 g, 38.96 mmol) and triethylsilane (28 mL, 175.3 mmol, d=0.728) in anhydrous CH2Cl2, then the reaction is allowed to gradually warm to ambient temperature over 3 h. The reaction is quenched with a saturated aqueous solution of sodium bicarbonate and extracted with additional CH2Cl2. The organic layer is dried, concentrated, and separated by chiral chromatography to provide the title compound (11.7 g, 96%). 1H NMR (400 MHz, CDCl3): δ 7.44-7.33 (m, 5H), 7.12 (d, 2H, J=6.85 Hz), 6.90 (d, 2H, J=6.85 Hz), 5.04 (s, 2H), 4.22-4.14 (m, 2H), 3.03 (d, 1H, J=13.69 Hz), 2.87 (d, 1H, J=13.69 Hz), 1.48 (s, 3H), 1.27 (t, 3H, J=7.34 Hz). Rf=0.60 in 50% acetone in hexanes.

Workup

  1. customThe reaction is quenched with a saturated aqueous solution of sodium bicarbonate
  2. extractionextracted with additional CH2Cl2
  3. customThe organic layer is dried
  4. concentrationconcentrated
  5. customseparated by chiral chromatography

Sources & evidence

ORD record
ord-833235c9f2a74e1ea95f4e943d93b219
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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