Nitrogen → Methyl 4-(naphthalen-2-ylmethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

HRID 601828Notes

Reaction equation

HRID 601828 reaction equation
O=[C:2]1[C:9]2[CH:8]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[NH:6][C:5]=2[CH2:4][CH2:3]1.C1C2C(=CC=CC=2)C=CC=1[Mg]Br.N#N.C[C:29]1[CH:30]=[C:31]([CH:45]=[CH:46][C:47]=1C)/[CH:32]=[C:33]1\CC[C:36]2NC(C(OC)=O)=[CH:39][C:40]\1=2>C1COCC1.[Pd].CCOCC>[CH:39]1[C:30]2[C:31](=[CH:45][CH:46]=[CH:47][CH:29]=2)[CH:32]=[CH:33][C:40]=1[CH2:36][CH:2]1[C:9]2[CH:8]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[NH:6][C:5]=2[CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 947NitrogenHCID 59180145Methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 67269053(E)-methyl 4-(3,4-dimethylbenzylidene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateHCID 178418423HCID 178418423, compound2×

Product 1

HCID 59180124Methyl 4-(naphthalen-2-ylmethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized in two steps. First, methyl 4-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (1.00 g, 5.58 mmol) was reacted with 2-naphthalenylmagnesium bromide (55 mL, 21 mmol) according to General Procedure 3. In this example, the 2-naphthalenylmagnesium bromide was first placed in a separate flask and the Et2O was blown off with N2. The residue was then dissolved in 50 mL THF, and added to the 4-oxo solution over 20 min via cannulae. The resulting exo-olefin ((E)-methyl 4-(naphthalen-2-ylmethylene)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate) was converted to the title compound by hydrogenation according to General Procedure 6 (with 10% Pd/C). The crude product was used in the next step without further purification. 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.16 (ddt, J=12.27, 8.77, 6.00, 6.00 Hz, 1H) 2.51-2.62 (m, 1H) 2.62-2.78 (m, 2H) 2.97 (d, J=7.61 Hz, 2H) 3.37-3.46 (m, 1H) 3.67-3.69 (m, 3 H) 6.27 (d, J=1.71 Hz, 1H) 7.40-7.52 (m, 3H) 7.73 (s, 1H) 7.81-7.91 (m, 3H) 10.47 (br. s, 1H).

Workup

  1. customThe title compound was synthesized in two steps
  2. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-e845a5ff92574000b2bc22767fe00a7e
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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