Hydrochloric Acid → 1-((3aR,4S,6aS)-4-aminohexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-methyl-2-phenylbutan-1-one hydrochloric acid salt

HRID 2363537Notes

Reaction equation

HRID 2363537 reaction equation
[CH3:1][CH:2]([CH3:28])[CH:3]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:4]([N:6]1[CH2:10][C@@H:9]2[C@@H:11]([NH:14]C(=O)OC(C)(C)C)[CH2:12][CH2:13][C@@H:8]2[CH2:7]1)=[O:5].[ClH:29].O1CCOCC1>CCOCC>[ClH:29].[NH2:14][C@@H:11]1[C@@H:9]2[C@@H:8]([CH2:7][N:6]([C:4](=[O:5])[CH:3]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:2]([CH3:28])[CH3:1])[CH2:10]2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66590911tert-butyl(3aR,4S,6aS)-2-(3-methyl-2-phenylbutanoyl)octahydrocyclopenta[c]pyrrol-4-ylcarbamate

Product 1

HCID 665909011-((3aR,4S,6aS)-4-aminohexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-methyl-2-phenylbutan-1-one hydrochloric acid salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

tert-Butyl(3aR,4S,6aS)-2-(3-methyl-2-phenylbutanoyl)octahydrocyclopenta[c]pyrrol-4-ylcarbamate (39 mg, 0.101 mmol) from Step C was combined with 4 M HCl in dioxane (5 mL, 20.00 mmol) in ether (5 mL). After about 2 hours, the solvent was removed in vacuo to give 1-((3aR,4S,6aS)-4-aminohexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-methyl-2-phenylbutan-1-one hydrochloric acid salt which was used in the next step without additional purification: MS (ESI+) m/z 287 (M+H)+.

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-02b034d125554e5dafa70dc355a9a590
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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