Dimethylformamide → Ammonia

HRID 1272164Notes

Reaction equation

HRID 1272164 reaction equation
C(OC([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]([CH2:22][OH:23])=[C:14]([F:24])[CH:13]=3)[CH2:9]1)=O)(C)(C)C.[H-].[Na+].[CH:27]1(Br)[CH2:29][CH2:28]1.[CH3:31]N(C)C=O>FC(F)(F)C(O)=O>[NH3:8].[CH:27]1([CH2:31][O:23][CH2:22][C:15]2[N:16]=[C:17]3[C:12](=[CH:13][C:14]=2[F:24])[CH2:11][C@H:10]2[N:18]3[C@H:19]([CH3:21])[CH2:20][NH:8][CH2:9]2)[CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 78037BromocyclopropaneHCID 69357319HCID 69357319, compound

Product 2

HCID 222AmmoniaHCID 69359454HCID 69359454, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (4R,9aR)-7-fluoro-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 3.3 mL dimethylformamide was added portionwise 0.100 g sodium hydride (55% in oil) and 0.27 g cyclopropyl bromide and the mixture was stirred at room temperature for 8 h. The reaction mixture was partitioned between water and ethyl acetate and the concentrated organic phase was purified by chromatography on silica gel with heptane:ethyl acetate=1:1 to yield 0.144 g of a slightly yellow oil which was taken up in 1.5 mL trifluoroacetic acid and kept at room temperature for 1 h. The solvent was evaporated and the residue was purified by chromatography on silica gel with dichloromethane:methanol:satd. ammonia (9:1:0.1) to yield 0.095 g (4R,9aR)-6-cyclopropylmethoxymethyl-7-fluoro-4-methyl-1,2,3,4,9,9a-hexahydro-2,4a,5-triaza-fluorene as a yellow orange oil.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customthe concentrated organic phase was purified by chromatography on silica gel with heptane
  3. customethyl acetate=1:1 to yield 0.144 g of a slightly yellow oil which
  4. waitkept at room temperature for 1 h
  5. customThe solvent was evaporated
  6. customthe residue was purified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-02661c56f7674c878e068c41e7fc6774
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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