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 1884066Notes

Reaction equation

HRID 1884066 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-918eab8943b54cc5a11a7741ca3ad3c7
Source dataset
uspto-grants-2004_07
Patent number
US06762301B2

Reaction notes

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