HCID 20355557, compound → 67838-56-6

HRID 225422Notes

Reaction equation

HRID 225422 reaction equation
C([O:8][CH2:9][CH:10]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[NH:11]1)C1C=CC=CC=1>C(OC(C)=O)(C)C.[Pd]>[OH:8][CH2:9][CH:10]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[NH:11]1

Participants

4

Reactant 1

HCID 20355557HCID 20355557, compound

Product 1

HCID 2035555967838-56-6Yield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7915Isopropyl AcetateSolvent2×

Procedure

Dioxide 7 (40 g, 0.17 mol) was placed in the glass liner within a 2 L Parr hydrogenator and dissolved in a mixture of IMS (150 ml) and iPrOAc (150 ml). A suspension of 5% palladium on carbon (Johnson Matthey type 392, 18 g) in iPrOAc (50 mL) was added and the suspension stirred under a hydrogen atmosphere of 70 psi for 3 days. After this time an NMR IPC was carried out that showed approx 15% benzylated material still present. After a further 4 days the reaction was 94% complete and it was decided to stop the hydrogenolysis. The palladium catalyst was filtered under nitrogen on a bed of celite, which was subsequently washed with IMS (250 mL) and iPrOAc (250 mL). The filtrate and washings were concentrated to give the crude product as an oil (26.26 g). The oil was purified by flash column chromatography (silica gel, DCM/methanol (9:1)) yielding 16.65 g (67%) of the hydroxyl-dioxide 8 as a white solid.

Workup

  1. additionwas added
  2. waitAfter a further 4 days the reaction was
  3. filtrationThe palladium catalyst was filtered under nitrogen on a bed of celite, which
  4. washwas subsequently washed with IMS (250 mL) and iPrOAc (250 mL)
  5. concentrationThe filtrate and washings were concentrated
  6. customto give the crude product as an oil (26.26 g)
  7. customThe oil was purified by flash column chromatography (silica gel, DCM/methanol (9:1))

Sources & evidence

ORD record
ord-2a786ed7b2e54904bcebd00e19146709
Source dataset
uspto-grants-2009_07
Patent number
US07557095B2

Reaction notes

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