Methyl 3-(benzyloxy)-6-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboxylate → Methyl 3-hydroxy-6-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboxylate

HRID 873529Notes

Reaction equation

HRID 873529 reaction equation
C([O:8][C:9]1[C:10]([C:44]([O:46][CH3:47])=[O:45])=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([CH:23]3[C:36]4[C:35](=[O:37])[CH2:34][C:33]([CH3:39])([CH3:38])[CH2:32][C:31]=4[O:30][C:29]4[CH2:28][C:27]([CH3:41])([CH3:40])[CH2:26][C:25](=[O:42])[C:24]3=4)[C:16]=2[CH3:43])=[CH:13][CH:14]=1)C1C=CC=CC=1>[C].[Pd].C1COCC1>[OH:8][C:9]1[C:10]([C:44]([O:46][CH3:47])=[O:45])=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([CH:23]3[C:24]4[C:25](=[O:42])[CH2:26][C:27]([CH3:40])([CH3:41])[CH2:28][C:29]=4[O:30][C:31]4[CH2:32][C:33]([CH3:39])([CH3:38])[CH2:34][C:35](=[O:37])[C:36]3=4)[C:16]=2[CH3:43])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 117700825Methyl 3-(benzyloxy)-6-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboxylate

Product 1

HCID 117700763Methyl 3-hydroxy-6-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboxylateYield 95.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 10% palladium carbon catalyst (wet) (3.15 g) was added to a solution of the methyl 3-(benzyloxy)-6-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboxylate produced in Example 11-2 (3.15 g, 4.95 mmol) in THF (63 ml) at room temperature, and the mixture thus obtained was then stirred under a hydrogen atmosphere at room temperature for 3 hours. A solid was removed from the reaction solution by filtration, and the solvent was then distilled away from the filtrate thus obtained under reduced pressure to obtain the title compound (2.58 g, yield: 95%).

Workup

  1. customthe mixture thus obtained
  2. customA solid was removed from the reaction solution by filtration
  3. distillationthe solvent was then distilled away from the filtrate
  4. customthus obtained under reduced pressure

Sources & evidence

ORD record
ord-61515acae8d140978bb87964550c86e4
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

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