Acetic Acid → (4R,9aR)-6-chloro-7-ethoxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

HRID 1272104Notes

Reaction equation

HRID 1272104 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C:10](=[CH:11][C:12]3[C:17]2=[N:16][C:15]([Cl:22])=[C:14]([O:23][CH2:24][CH3:25])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.C(=O)(O)[O-].[Na+]>>[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]([Cl:22])=[C:14]([O:23][CH2:24][CH3:25])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 86596339(R)-6-chloro-7-ethoxy-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Product 1

HCID 86596344(4R,9aR)-6-chloro-7-ethoxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl esterYield 96.8%

Procedure

To a solution of 0.30 g (0.82 mmol) (R)-6-chloro-7-ethoxy-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 6 mL acetic acid 0.26 g (4.10 mmol) sodium cyanoborohydride was added. After 1 h the reaction was poured into 10% aqueous sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography over silica gel with ethyl acetate:n-hexane (1:2) as eluant to yield the product as a light yellow oil (96.8%).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel with ethyl acetate:n-hexane (1:2) as eluant

Sources & evidence

ORD record
ord-2d2df848fbf7421ca8f1f0119f19cff7
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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