Tert-butyl 3-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-3-hydroxypentanoate → Tert-butyl 3-hydroxy-3-[3-(hydroxymethyl)-2-methoxy-4-pyridinyl]pentanoate

HRID 720493Notes

Reaction equation

HRID 720493 reaction equation
C([O:8][CH2:9][C:10]1[C:11]([O:28][CH3:29])=[N:12][CH:13]=[CH:14][C:15]=1[C:16]([OH:27])([CH2:25][CH3:26])[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])C1C=CC=CC=1>[Pd].C(O)C>[OH:27][C:16]([C:15]1[CH:14]=[CH:13][N:12]=[C:11]([O:28][CH3:29])[C:10]=1[CH2:9][OH:8])([CH2:25][CH3:26])[CH2:17][C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19]

Participants

4

Reactant 1

HCID 10834902Tert-butyl 3-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-3-hydroxypentanoate

Product 1

HCID 21891952Tert-butyl 3-hydroxy-3-[3-(hydroxymethyl)-2-methoxy-4-pyridinyl]pentanoateYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl 3-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-3-hydroxypentanoate (1 g, 2.5 mmol) is subjected to hydrogenolysis at atmospheric pressure and at ambient temperature using 5% palladium on carbon as catalyst (50 mg) and absolute ethanol as solvent (10 ml). Once the reaction has terminated (6 hours), the catalyst is separated by filtration and the solvent is evaporated off, which leaves 0.7 g (90%) of product (K) of a sufficient purity for a subsequent synthetic use.

Workup

  1. customis subjected to hydrogenolysis at atmospheric pressure and at ambient temperature
  2. customOnce the reaction has terminated (6 hours)
  3. customthe catalyst is separated by filtration
  4. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-215f11e032b04799ae6aa65519420b6a
Source dataset
uspto-grants-2006_11
Patent number
US07135478B2

Reaction notes

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