HCID 66747402, compound → HCID 66747249, compound

HRID 931368Notes

Reaction equation

HRID 931368 reaction equation
[OH:1][B:2]1[CH2:7][CH:6]=[CH:5][CH:4]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[O:3]1>CCOC(C)=O.[Pd]>[OH:1][B:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[O:3]1

Participants

4

Reactant 1

HCID 66747402HCID 66747402, compound

Product 1

HCID 66747249HCID 66747249, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2-(2-hydroxy-3,6-dihydro-2H-1,2-oxaborinin-6-yl)acetate XLVII (670 mg, 3.16 mmol) in EtOAc (45 mL) was added 10% Pd/C (135 mg). The vessel was evacuated by applying vacuum and flushed with hydrogen gas. The reaction was stirred under hydrogen for 2 h. The mixture was filtered through a Celite pad and which was washed with additional EtOAc (15 mL). Concentration of the filtrate gave pure tert-butyl 2-(2-hydroxy-1,2-oxaborinan-6-yl)acetate XLVIII (641 mg, 3.00 mmol, 94.8% yield).

Workup

  1. customThe vessel was evacuated
  2. customflushed with hydrogen gas
  3. filtrationThe mixture was filtered through a Celite pad and which
  4. washwas washed with additional EtOAc (15 mL)

Sources & evidence

ORD record
ord-7b77143c55c54b359bef99415a8b99d0
Source dataset
uspto-grants-2016_03
Patent number
US09296763B2

Reaction notes

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