Dimethylformamide → HCID 69357852, compound

HRID 1272153Notes

Reaction equation

HRID 1272153 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]([C@H:22]([OH:24])[CH3:23])=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25]N(C)C=O.CI.[Cl-].[NH4+]>>[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]([C@H:22]([O:24][CH3:25])[CH3:23])=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 67237861(4R,9aR)-6-(1-(R)-hydroxy-ethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Product 1

HCID 69357852HCID 69357852, compound

Procedure

To a solution of 0.75 g (2.25 mmol) (4R,9aR)-6-(1-(R)-hydroxy-ethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 5 mL N,N-dimethylformamide 0.12 g (2.70 mmol) sodium hydride (55–65% dispersion in oil) was added. After 30 min., 0.28 mL (0.64 g, 4.50 mmol) methyl iodide was added and the reaction mixture was stirred at 50 deg C. for 2 h. After cooling down to room temperature, the reaction mixture was poured into 10% aqueous ammonium chloride 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 on silica gel (0.032–0.063 mm) with ethyl acetate:n-heptane (1:2) as eluant.

Workup

  1. waitfor 2 h
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (0.032–0.063 mm) with ethyl acetate:n-heptane (1:2) as eluant

Sources & evidence

ORD record
ord-e33ba8a3222944e78f8ebcb9c6f6252f
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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