HCID 86642747, compound → HCID 67017852, compound

HRID 1015548Notes

Reaction equation

HRID 1015548 reaction equation
C(OC(=O)[NH:10][C:11]12[CH2:18][CH:17]3[CH2:19][C:13]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:30][CH2:29][CH2:28][C:27]5=[O:31])=[CH:22][CH:21]=4)([CH2:14][CH:15]1[CH2:16]3)[CH2:12]2)C1C=CC=CC=1>CO.[Pd]>[NH2:10][C:11]12[CH2:18][CH:17]3[CH2:19][C:13]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:30][CH2:29][CH2:28][C:27]5=[O:31])=[CH:22][CH:21]=4)([CH2:14][CH:15]1[CH2:16]3)[CH2:12]2

Participants

4

Reactant 1

HCID 86642747HCID 86642747, compound

Product 1

HCID 67017852HCID 67017852, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl[2-[4-(2-Oxopyrrolidin-1-yl)phenyl)hexahydro-2,5-methanopentalene-3a(1H)-yl]carbamate (0.73 g, 1.7 mmol) obtained in step I and Pd/C (10%, 0.4 g) in MeOH (17 mL) was stirred at room temperature under H2 atmosphere for 2 h. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure to obtain 1-[4-(3-aminotricyclo[3.3.1.03,7]non-1-yl)phenyl]pyrrolidin-2-one as an off-white solid (0.43 g, 85% yield). m/z (M+1) 297; 1H NMR (CDCl3) 300 MHz δ 7.52 (d, J=8.6 Hz, 2H), 7.25 (d, J=8.6 Hz, 2H), 3.86 (t, J=6.9 Hz, 2H), 2.62 (t, J=7.9 Hz, 2H), 2.52-2.42 (m, 1H), 2.32-1.60 (m, 13H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-eb7ddfb98134466897ee20798e2602e7
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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