HCID 12082209, compound → HCID 22663109, compound

HRID 392120Notes

Reaction equation

HRID 392120 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([CH:26]=O)=[C:20]([N+:23]([O-])=O)[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[O:18][C:17]3[C:19]([CH3:26])=[C:20]([NH2:23])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 12082209HCID 12082209, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22663109HCID 22663109, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

[(2R)-8-Formyl-7-nitro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methyl-benzenesulfonate (1.4 g, 2.74 mmole) in methanol (40 mL) was was treated with 60 psi of hydrogen on a Parr shaker in the presence of 0.10 g 20% palladium hydroxide on carbon (Pearlman's catalyst) for 24 hours. The catalyst was removed by filtration and washed with methanol. The filtrate was evaporated in vacuum to give 0.94 g (93%) of the (R)-enantiomer of the title compound as a beige solid. 1H (DMSO) broad singlet 10.0 δ (2 H); doublet 7.8 δ (2 H); doublet 7.5 δ (2 H); doublet 6.9 δ (1H); doublet 6.8 δ (2 H); multiplet 4.0-4.6 δ (5 H); singlet 2.4 δ (3 H); singlet 2.1 δ (3 H).

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol
  3. customThe filtrate was evaporated in vacuum

Sources & evidence

ORD record
ord-60ff74d5af4542f5950b095f4f2b5db1
Source dataset
uspto-grants-2004_10
Patent number
US06800641B2

Reaction notes

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