Ammonia → HCID 69337262, compound

HRID 1295353Notes

Reaction equation

HRID 1295353 reaction equation
[Na].N.[C:3]([O:7][C:8](=[O:33])[N:9]([CH3:32])[C@:10]12[CH2:15][C@H:14]1[CH2:13][N:12](S(C1C=CC(C)=CC=1)(=O)=O)[C@H:11]2[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:6])([CH3:5])[CH3:4].[Cl-].[NH4+]>C1COCC1>[C:3]([O:7][C:8](=[O:33])[N:9]([CH3:32])[C@:10]12[CH2:15][C@H:14]1[CH2:13][NH:12][C@H:11]2[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 69432033HCID 69432033, compound

Product 1

HCID 69337262HCID 69337262, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flame dried 125 mL rbf equipped with a dry ice condenser was added fresh sodium metal (0.32 g, 14.0 mmol). The flask was immersed in a −78° C. bath and ammonia gas was condensed into the flask until it was about a third full. Racemic Intermediate 11, one enantiomer being methyl-[(1R,2S,5S)-2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl ester (0.62 g, 1.4 mmol) in THF (10 mL) was added to the flask in a thin constant stream and the mixture was stirred for 10 minutes until the reaction was complete. Solid ammonium chloride was added and the reaction was warmed to room temperature. The volatile solvents were allowed to evaporate and the residue was partitioned between 1N NaOH and methylene chloride. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound as an oil (0.40 g, quantitative yield).

Workup

  1. customTo a flame dried 125 mL
  2. customrbf equipped with a dry ice condenser
  3. customwas immersed in a −78° C.
  4. customcondensed into the flask until it
  5. additionwas added to the flask in a thin constant stream
  6. customto evaporate
  7. customthe residue was partitioned between 1N NaOH and methylene chloride
  8. washThe organics were washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-69e358e2d3a643cf815b761f77a92063
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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