HCID 54674341, compound → HCID 54674493, compound

HRID 2402744Notes

Reaction equation

HRID 2402744 reaction equation
C([NH:8][C@@:9]1([CH3:27])[C@@H:16]2[C@@H:12]([CH2:13][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[N:18]=3)[CH2:15]2)[CH2:11][CH2:10]1)C1C=CC=CC=1.[H][H]>C(O)(C)C>[CH3:27][C@:9]1([NH2:8])[C@@H:16]2[C@@H:12]([CH2:13][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[N:18]=3)[CH2:15]2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 54674341HCID 54674341, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54674493HCID 54674493, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(3aR,4R,6aS)—N-Benzyl-4-methyl-2-[6-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-amine (30 mg, 0.080 mmol) from Example 21 and isopropanol (14 mL) were added to 20% Pd(OH)2—C, wet (6.0 mg, 0.043 mmol) in a 50 mL pressure bottle and stirred for 90 minutes under 30 psi hydrogen gas at 50° C. The mixture was filtered through a nylon membrane and the solvent was removed in vacuo. The crude material was purified by silica gel chromatography using 1-10% methanol (2 N ammonia)/dichloromethane as eluent to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.54-7.46 (m, 1H), 6.97 (d, J=7.2, 1H), 6.52 (d, J=8.6, 1H), 3.75 (dd, J=11.3, 5.2, 1H), 3.56 (dd, J=10.3, 8.4, 1H), 3.52-3.43 (m, 1H), 3.36 (dd, J=10.5, 3.9, 1H), 2.72-2.62 (m, 1H), 2.31 (td, J=8.7, 5.3, 1H), 1.92-1.81 (m, 1H), 1.77-1.68 (m, 1H), 1.60-1.35 (br m, 2H), 1.54-1.42 (m, 2H), 1.16 (s, 3H); MS (ESI+) m/z 286 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. customthe solvent was removed in vacuo
  3. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d4691df662f04c8e95a64eab4b25fcfa
Source dataset
uspto-grants-2014_08
Patent number
US08796470B2

Reaction notes

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