Acetic Acid → (3aS*,4S*,6aR*)-2-benzyl-N-cyclopropyloctahydrocyclopenta[c]pyrrol-4-amine

HRID 2363527Notes

Reaction equation

HRID 2363527 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]2[C:13](=O)[CH2:14][CH2:15][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]1([NH2:20])[CH2:19][CH2:18]1.C(O)(=O)C.C([BH3-])#N>ClCCl>[CH2:1]([N:8]1[CH2:12][C@H:11]2[C@@H:13]([NH:20][CH:17]3[CH2:19][CH2:18]3)[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

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 498716Cyano-borohydrideHCID 134637692-Benzylhexahydrocyclopenta[c]pyrrol-4(1H)-one

Product 1

HCID 46213241(3aS*,4S*,6aR*)-2-benzyl-N-cyclopropyloctahydrocyclopenta[c]pyrrol-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Benzylhexahydrocyclopenta[c]pyrrol-4(5H)-one (0.578 g, 2.68 mmol), cyclopropylamine (0.189 mL, 2.68 mmol), and acetic acid (10 mL) were combined in dichloromethane (20 mL). PS-Cyanoborohydride (1.147 g, 2.68 mmol) was added. The reaction was stirred at room temperature for 2 hours, then filtered and the resin was washed with dichloromethane. The solvent was removed in vacuo, and the crude material was applied to a silica gel column and was eluted with 1-10% methanol (2 N ammonia)/dichloromethane to give the title compounds.

Workup

  1. filtrationfiltered
  2. washthe resin was washed with dichloromethane
  3. customThe solvent was removed in vacuo
  4. washwas eluted with 1-10% methanol (2 N ammonia)/dichloromethane

Sources & evidence

ORD record
ord-7e6147fc55034dd69b9d9924fdd68a34
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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