Dichloromethane → HCID 67017823, compound

HRID 1015573Notes

Reaction equation

HRID 1015573 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]34[CH2:29][CH:17]5[CH2:18][C:19]([NH:21]C(=O)OC(C)(C)C)([CH2:20]3)[CH:15]([CH2:16]5)[CH2:14]4)=[CH:9][CH:8]=2)[C:3]1=[O:30].C(Cl)Cl>[Pd].CO>[NH2:21][C:19]12[CH2:18][CH:17]3[CH2:29][C:13]([C:10]4[CH:9]=[CH:8][C:7]([N:4]5[CH2:5][CH2:6][N:2]([CH3:1])[C:3]5=[O:30])=[CH:12][CH:11]=4)([CH2:14][CH:15]1[CH2:16]3)[CH2:20]2

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 86761377HCID 86761377, compound

Product 1

HCID 67017823HCID 67017823, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of the compound obtained from step I (0.25 g, 0.56 mmol) in a 1:1-mixture of CH2Cl2 and MeOH (10 mL) was added Pd/C (10% w/w, 0.1 g) and 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-(3a-aminohexahydro-2,5-methanopentalen-2(1H)-yl)phenyl]-3-methylimidazolidin-2-one (0.15 g) as an off-white solid in 86% yield. M.R. 227-230° C.; m/z (M+1), 312; IR cm-1 3416, 3249, 2964, 1682, 1519, 1485, 1261, 810; 1H NMR (CDCl3+DMSO-d6) 300 MHz δ 8.38 (bs, 2H), 7.47 (d, J=8.6 Hz, 2H), 7.19 (d, J=8.6 Hz, 2H), 3.76 (t, J=7.4 Hz, 2H), 3.43 (t, J=7.4 Hz, 2H), 2.77 (s, 3H), 2.48-2.40 (m, 2H), 2.22-2.14 (m, 1H), 2.10-2.0 (m, 2H), 2.0-1.86 (m, 4H), 1.80-1.60 (m, 3H).

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-7a10f45e2a4f41768924089d2b05309f
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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