(4R,9aR)-6-Benzyloxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester → HCID 178418747, compound

HRID 11934Notes

Reaction equation

HRID 11934 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([O:22]CC2C=CC=CC=2)=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([OH:22])=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 69359127(4R,9aR)-6-Benzyloxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Product 1

HCID 178418747HCID 178418747, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 3.90 g (9.86 mmol) (4R,9aR)-6-benzyloxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 21, intermediate) in 30 ml methanol:ethyl acetate (1:1 v/v) 0.20 g 10% palladium on charcoal was added and the reaction was hydrogenated at atmospheric pressure for 2 h. After filtration over dicalite speed plus the filtrate was evaporated and the residue was chromatographed on silica gel (0.032–0.063 mm) with ethyl acetate:n-hexane (1:1) as eluant to afford the desired compound as a colorless foam (82.0%).

Workup

  1. filtrationAfter filtration over dicalite speed
  2. customthe filtrate was evaporated
  3. customthe residue was chromatographed on silica gel (0.032–0.063 mm) with ethyl acetate:n-hexane (1:1) as eluant

Sources & evidence

ORD record
ord-4de5f69c09a8424fa4014c420cfd14c6
Source dataset
uspto-grants-2006_08
Patent number
US07098337B2

Reaction notes

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