Hydrochloric Acid → (3aR,4S,6aS)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine

HRID 2363577Notes

Reaction equation

HRID 2363577 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:13][C@@H:12]3[C@@H:14]([NH:17]C(=O)OC(C)(C)C)[CH2:15][CH2:16][C@@H:11]3[CH2:10]2)=[N:7][CH:8]=1.Cl.O1CCOCC1>>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:13][C@@H:12]3[C@@H:14]([NH2:17])[CH2:15][CH2:16][C@@H:11]3[CH2:10]2)=[N:7][CH:8]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66590375tert-butyl(3aR,4S,6aS)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-ylcarbamate

Product 1

HCID 66590965(3aR,4S,6aS)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine

Procedure

tert-butyl(3aR,4S,6aS)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-ylcarbamate (282 mg, 0.759 mmol) from Step A was combined with 4 N HCl in 1,4-dioxane (2.5 mL, 9.87 mmol). The reaction was stirred at room temperature overnight and then the volatiles were removed in vacuo. The compound was purified using a 12 g silica gel cartridge eluting with a gradient of 0-7.5% methanol (2 N ammonia)/dichloromethane over 20 minutes to give (3aR,4S,6aS)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.64 (s, 1H), 7.69 (dd, J=8.9, 2.5, 1H), 6.38 (d, J=8.9, 1H), 4.95 (s, 2H), 3.56 (dd, J=23.7, 14.1, 3H), 3.25 (d, J=6.2, 1H), 3.11 (q, J=6.0, 1H), 2.83-2.68 (m, 1H), 2.35 (ddd, J=13.1, 7.9, 5.3, 1H), 2.02 (dtd, J=13.5, 8.3, 5.5, 1H), 1.92 (ddd, J=18.3, 7.4, 5.6, 1H), 1.46-1.30 (m, 2H); MS (ESI+) m/z 272 (M+H)+.

Workup

  1. customthe volatiles were removed in vacuo
  2. customThe compound was purified
  3. washeluting with a gradient of 0-7.5% methanol (2 N ammonia)/dichloromethane over 20 minutes

Sources & evidence

ORD record
ord-2a5063c23fc14135b6d6c77da7fa5657
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

Loading…