Water → HCID 22866039, compound

HRID 863769Notes

Reaction equation

HRID 863769 reaction equation
[CH2:1]([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15](OCC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC.O>C1COCC1.[NH4+].[OH-]>[CH2:1]([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 56990325HCID 56990325, compound

Product 1

HCID 22866039HCID 22866039, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of (1S,4S)-2-benzyl-5-ethoxycarbonyl-2,5-diazabicyclo(2.2.1)heptane (3.3 g, 0.013 mol) in THF at -10° C., was added dropwise 1M LiAlH4 in ether (26.3 mL, 0.026 mol). The reaction mixture was slowly warmed to room temperature and mixed overnight. Upon cooling to 0° C., 4 mL of 95% THF:H2O was slowly added followed by 4 mL of H2O. The mixture was diluted with NH4OH (40 mL), filtered through a celite pad and concentrated in vacuo. The remaining NH4OH solution was further diluted with NH4OH (15 mL) and extracted with CH2Cl2. The combined organic phases were dried (K2CO3) and concentrated in vacuo to yield (1S,4S)-2-benzyl-5-methyl-2,5-diazabicyclo(2.2.1)heptane (2.2 g, 86%).

Workup

  1. additionmixed overnight
  2. temperatureUpon cooling to 0° C.
  3. filtrationfiltered through a celite pad
  4. concentrationconcentrated in vacuo
  5. additionThe remaining NH4OH solution was further diluted with NH4OH (15 mL)
  6. extractionextracted with CH2Cl2
  7. dry with materialThe combined organic phases were dried (K2CO3)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f457cd33d1446e4bceb1359ac9f40f7
Source dataset
uspto-grants-1996_10
Patent number
US05561127

Reaction notes

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