HCID 69256696, compound → (R)-2,3-dihydro-1,4-dioxino[2,3-b]-pyridine-3-methanol

HRID 30089Notes

Reaction equation

HRID 30089 reaction equation
C1(C[O:8][CH2:9][CH:10]2[O:19][C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[O:12][CH2:11]2)C=CC=CC=1.[H][H]>CO.[Pd]>[O:12]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[O:19][C@@H:10]([CH2:9][OH:8])[CH2:11]1.[O:12]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[O:19][C@H:10]([CH2:9][OH:8])[CH2:11]1

Participants

6

Reactant 2

HCID 69256696HCID 69256696, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 11535620(R)-2,3-dihydro-1,4-dioxino[2,3-b]-pyridine-3-methanolHCID 69255535HCID 69255535, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2,3-dihydro-3-[(phenylmethoxy)methyl]-1,4-dioxino[2,3-b]pyridine (0.0638 mol) in CH3OH (250 ml) was hydrogenated with palladium-on-carbon (10%, 2 g) as a catalyst. After uptake of hydrogen (1 equivalent), the catalyst was filtered off and the filtrate was evaporated. This fraction was purified by HPLC (eluent ethanol/methanol 60/40; column: Chiralpak AD 20 μm). Two fractions were collected and the solvent was evaporated, yielding 4.06 g of (S)-2,3-dihydro-1,4-dioxino[2,3-b]-pyridine-3-methanol (intermediate 2-a) ([α]D20=−34.33°; c=25.34 mg/5 ml in methanol) and 3.81 g of (R)-2,3-dihydro-1,4-dioxino[2,3-b]-pyridine-3-methanol (intermediate 2-b) ([α]D20=+32.740; c=22.60 mg/5 ml in methanol).

Workup

  1. customthe filtrate was evaporated
  2. customThis fraction was purified by HPLC (eluent ethanol/methanol 60/40; column: Chiralpak AD 20 μm)
  3. customTwo fractions were collected
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4f6df2d8ae504083be4568fb411ac3cb
Source dataset
uspto-grants-2008_09
Patent number
US07423048B2

Reaction notes

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