Ammonia → HCID 69336084, compound

HRID 1295377Notes

Reaction equation

HRID 1295377 reaction equation
[Na].N.[C:3]([O:7][C:8](=[O:32])[NH:9][C@@:10]12[CH2:15][CH: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]>C1COCC1>[C:3]([O:7][C:8](=[O:32])[NH:9][C@@:10]12[CH2:15][CH: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])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 69342316[(1S,2S)-2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl ester

Product 1

HCID 69336084HCID 69336084, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flame dried 250 mL rbf equipped with a dry ice condenser was added fresh sodium metal (0.32 g, 14 mmol). The flask was immersed in a −78° C. bath and ammonia gas was condensed into the flask (˜30 mL). Racemic Intermediate 47, one enantiomer being [(1S,2S)-2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl ester (3.0 g, 7.0 mmol) in THF (7 mL, 2 mL rinse) was added to the flask in a fast dropwise fashion and the thick mixture was stirred for 5 minutes at which point tic indicated the reaction was complete. The reaction was warmed to room temperature and volatile solvents allowed to evaporate. The residue was partitioned between H2O and methylene chloride, the organics were washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound as a foam (1.9 g, quantitative yield).

Workup

  1. customTo a flame dried 250 mL
  2. customrbf equipped with a dry ice condenser
  3. customwas immersed in a −78° C.
  4. customcondensed into the flask (˜30 mL)
  5. additionwas added to the flask in a fast dropwise fashion
  6. customto evaporate
  7. customThe residue was partitioned between H2O 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-5ae68806bb3b418193aff8ef7d20012c
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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