Hydrochloric Acid → (3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine

HRID 2363565Notes

Reaction equation

HRID 2363565 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([S:9]([N:12]2[CH2:16][C@@H:15]3[C@@H:17]([NH:20]C(=O)OC(C)(C)C)[CH2:18][CH2:19][C@@H:14]3[CH2:13]2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.Cl>C(O)C>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:4]=[C:5]([S:9]([N:12]2[CH2:16][C@@H:15]3[C@@H:17]([NH2:20])[CH2:18][CH2:19][C@@H:14]3[CH2:13]2)(=[O:10])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66590472tert-butyl(3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylcarbamate

Product 1

HCID 66590521(3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl(3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylcarbamate (0.814 g, 1.874 mmol) from Step C and HCl (26.2 mL, 52.5 mmol, 2 M in ether) in ethanol (3 mL) were combined. The reaction was stirred at room temperature overnight and then the volatiles were removed. The compound was purified using a 24 g silica gel cartridge with a gradient of 1-10% methanol (2 N ammonia)/dichloromethane over 20 minutes to give (3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.37 (s, 1H), 8.21 (d, J=7.9, 1H), 7.93 (d, J=7.9, 1H), 7.75 (t, J=7.9, 1H), 3.41 (dd, J=9.8, 2.8, 1H), 3.13 (dd, J=9.7, 3.1, 1H), 3.03-2.98 (m, 1H), 2.97-2.89 (m, 2H), 2.56-2.45 (m, 1H), 2.14 (tdd, J=8.7, 5.9, 2.9, 1H), 1.5-2.0 (m, 2H) 1.95-1.85 (m, 1H), 1.79-1.69 (m, 1H), 1.32-1.15 (m, 2H); MS (ESI+) m/z 335 (M+H)+.

Workup

  1. customthe volatiles were removed
  2. customThe compound was purified
  3. customover 20 minutes

Sources & evidence

ORD record
ord-a88084c4c05840078e5ad66cb9b1eb95
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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