HCID 86642748, compound → HCID 59374965, compound

HRID 1015550Notes

Reaction equation

HRID 1015550 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[CH:30]=[CH:29][CH:28]=[CH:27]5)=[CH:22][CH:21]=4)([CH2:14][CH:15]1[CH2:16]3)[CH2:12]2)C1C=CC=CC=1>CO>[N:26]1([C:23]2[CH:22]=[CH:21][C:20]([C:13]34[CH2:19][CH:17]5[CH2:18][C:11]([NH2:10])([CH2:12]3)[CH:15]([CH2:16]5)[CH2:14]4)=[CH:25][CH:24]=2)[CH:30]=[CH:29][CH:28]=[CH:27]1

Participants

3

Reactant 1

HCID 86642748HCID 86642748, compound

Product 1

HCID 59374965HCID 59374965, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of the compound obtained from step I (0.8 g, 1.94 mmol) in MeOH (20 mL) Pd/C (10%, 0.1 g) was added. The reaction mixture was stirred at r.t. for 2 h under H2 pressure with a balloon. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure to obtain 2-[4-(1H-pyrrol-1-yl)phenyl]hexahydro-2,5-methanopentalen-3a(1H)-amine (0.45 g) as a viscous liquid (0.45 g) in 83% yield. m/z (M+1) 279; 1H NMR (CD3OD) 300 MHz δ 7.40-7.25 (m, 4H), 7.20-7.05 (m, 2H), 6.30-6.20 (m, 2H), 2.57-2.46 (m, 1H), 2.46-2.38 (m, 1H), 2.30-2.13 (m, 2H), 2.13-1.81 (m, 7H), 1.80-1.70 (m, 1H).

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-8cc67c551d374054a89251539082af30
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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