Aluminium lithium hydride → (3aR,4S,6aS)-2-benzyl-N-methyloctahydrocyclopenta[c]pyrrol-4-amine

HRID 2363534Notes

Reaction equation

HRID 2363534 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]2[C@@H:13]([NH:16][C:17](=O)OC(C)(C)C)[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:8]1[CH2:12][C@@H:11]2[C@@H:13]([NH:16][CH3:17])[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66590514tert-butyl(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylcarbamate

Product 1

HCID 66591269(3aR,4S,6aS)-2-benzyl-N-methyloctahydrocyclopenta[c]pyrrol-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylcarbamate (59 mg, 0.187 mmol) from Step A was treated with lithium aluminum hydride (0.374 mmol) in tetrahydrofuran (0.5 mL). The reaction was stirred at room temperature for 1 hour and then heated to reflux for 2 hours. The reaction was cooled to room temperature and quenched with dropwise addition of saturated aqueous sodium sulfate (50 μL) to give a precipitate. The precipitate was washed with tetrahydrofuran, and then the solvent was removed to give (3aR,4S,6aS)-2-benzyl-N-methyloctahydrocyclopenta[c]pyrrol-4-amine: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.34-7.28 (m, 4H), 7.25-7.19 (m, 1H), 3.60-3.51 (m, 2H), 2.76 (q, J=5.6, 1H), 2.64 (d, J=15.7, 1H), 2.58-2.53 (m, 1H), 2.51-2.46 (m, 1H), 2.40-2.35 (m, 4H), 2.31-2.22 (m, 2H), 1.98-1.85 (m, 2H), 1.39 (dt, J=5.7, 10.6, 3H); MS (ESI+) m/z 231 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. temperatureThe reaction was cooled to room temperature
  4. customquenched with dropwise addition of saturated aqueous sodium sulfate (50 μL)
  5. customto give a precipitate
  6. washThe precipitate was washed with tetrahydrofuran
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-8e8219a3a6a94a2a9f286df6bd5c8b04
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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