Hydrochloric Acid → (3AS,4S,6AR)-2-Benzyloctahydrocyclopenta[C]pyrrol-4-amine

HRID 2363443Notes

Reaction equation

HRID 2363443 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]2[C@@H:13]([NH:16][S@](C(C)(C)C)=O)[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.Cl>CO>[CH2:1]([N:8]1[CH2:12][C@H:11]2[C@@H:13]([NH2:16])[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 313Hydrochloric AcidHCID 66590593(S)-N-((3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl)-2-methylpropane-2-sulfinamide

Product 1

HCID 25918979(3AS,4S,6AR)-2-Benzyloctahydrocyclopenta[C]pyrrol-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-N-((3aS,4S,6aR)-2-Benzyloctahydrocyclopenta[c]pyrrol-4-yl)-2-methylpropane-2-sulfinamide (855 mg, 2.67 mmol) from Step B and 2 N HCl (10 mL, 40.0 mmol) were combined in methanol (10 mL). After 30 minutes, the solvent was removed and the crude material was purified on a silica gel cartridge (Analogix®, Burlington, Wis., RS-25) loading with 10% methanol (2 N ammonia)/dichloromethane solution and eluting with 2-10% methanol (2 N ammonia)/dichloromethane to give (3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.44 (d, J=7.4, 2H), 7.36 (t, J=7.5, 2H), 7.28 (t, J=7.3, 1H), 3.52 (q, J=13.0, 2H), 3.29 (q, J=7.3, 1H), 2.84 (dd, J=3.7, 9.3, 1H), 2.55-2.43 (m, 3H), 2.37-2.30 (m, 1H), 2.24 (d, J=5.3, 1H), 1.74-1.64 (m, 2H), 1.62-1.53 (m, 1H), 1.34 (dd, J=5.0, 10.1, 1H).

Workup

  1. customthe solvent was removed
  2. customthe crude material was purified on a silica gel cartridge (Analogix®, Burlington, Wis., RS-25) loading with 10% methanol (2 N ammonia)/dichloromethane solution
  3. washeluting with 2-10% methanol (2 N ammonia)/dichloromethane

Sources & evidence

ORD record
ord-555bf1c844254078a15c09d634368a4c
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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