HCID 67082072, compound → HCID 67082071, compound

HRID 1987749Notes

Reaction equation

HRID 1987749 reaction equation
[C:1]([N:4]1[C@H:8]([C@H:9]([OH:12])[CH2:10][OH:11])[C@H:7]([OH:13])[CH:6]=[N:5]1)(=[O:3])[CH3:2]>[OH-].[OH-].[Pd+2].CO>[C:1]([N:4]1[C@H:8]([C@H:9]([OH:12])[CH2:10][OH:11])[C@@H:7]([OH:13])[CH2:6][NH:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 67082072HCID 67082072, compound

Product 1

HCID 67082071HCID 67082071, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Pearlmans catalyst (200 mg) was suspended in a solution of methanol with (3S,4S)-2-acetyl-1,5-dihydro-3-[(1S)-1,2-dihydroxyethyl]-4-hydroxy-pyrazole (18) (200 mg, 1.11 mmol) and stirred overnight under an atmosphere of hydrogen. The reaction was filtered through celite and the filtrated concentrated in vacuo to afford a crude oil. The crude product was purified by chromatography to afford 19 (85 mg, 43%) as a colourless oil. 1H NMR δ 4.64 (dd, J=5.7, 3.4 Hz, 1H), 3.90 (m, 2H), 3.61 (m, 2H), 3.36 (dd, J=11.7, 6.5 Hz, 1H), 2.71 (dd, J=11.7, 6.0 Hz, 1H), 2.18 (s, 3H). 13C NMR δ 174.5, 75.4, 72.7, 68.2, 65.2, 56.4, 21.5. HRMS (M+) calc. for C7H14N2O4: 190.0953. Found 190.0951.

Workup

  1. filtrationThe reaction was filtered through celite
  2. concentrationthe filtrated concentrated in vacuo
  3. customto afford a crude oil
  4. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-e20874df449e4533aac75e751438f074
Source dataset
uspto-grants-2009_06
Patent number
US07553839B2

Reaction notes

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