HCID 15521821, compound → cis-10-Methylamino-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinoline

HRID 2304554Notes

Reaction equation

HRID 2304554 reaction equation
[CH3:1][N:2]=[C:3]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][N:5]2[C:13](=O)[CH2:14][CH2:15][CH:4]12.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][NH:2][C@@H:3]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][N:5]2[CH2:13][CH2:14][CH2:15][C@@H:4]12

Participants

4

Reactant 2

HCID 15521821HCID 15521821, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 70148934cis-10-Methylamino-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolineYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The 10-methylimino-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-3-one (880 mg, 4.1 mmol) was dissolved in THF (12 mL) and added dropwise to a suspension of LAH (623 mg, 16.4 mmol) in THF (12 ml) at room temperature under nitrogen. The suspension was stirred at reflux for 15 hours, cooled, and quenched by the addition of H2O(0.88 mL), NaOH (1.5 N, 0.88 mL) and additional H2O(2.6 mL). The mixture was filtered and the filtrate was concentrated in vacuo to give cis-10-methylamino-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinoline as a dark oil (600 mg). Chromatography on silica gel with CH2Cl2/MeOH/NH4OH (95:4:1) provided the product as a dark red, viscous oil (547 mg). 1H NMR (CDCl3, 300 MHz): δ 7.52 (d, J=7.63 Hz, 1H), 7.25 (t, J=7.23, 14.47 Hz, 1H), 7.17 (t, J=7.76, 15.13 Hz, 1H), 7.09 (d, J=7.63 Hz, 1H), 4.03 (d, J=14.01 Hz, 1H), 3.79 (d, J=10.01 Hz, 1H), 3.62 (d, J=14.01 Hz, 1H), 3.17 (m, 1H), 2.58 (m, 1H), 2.47 (m, 1H), 2.41 (s, 3H), 2.28 (m, 1H), 1.87 (m, 1H0, 1.69 (m, 1H); 13C NMR (CDCl3): δ 137.24, 135.83, 126.63, 126.20 (2C), 64.92, 62.70, 55.85, 54.71, 32.33, 30.04, 21.57; IR (neat): 3285 (br), 3060, 3020, 2950, 2870, 2795, 1735-1565 (br), 1475, 1450, 1155, 1035, 920, 905, 780, 720 cm−1; MS (FAB): m/e 203 (M+H, 74.8%), 201 (74.1%), 172 (M−NHMe, 100%), 170 (85%), 133 (53.1%), 132 (27%), 118 (17.7%); HRMS (FAB): Calc for C13H18N2 202.1469, found 203.1555 (M+H).

Workup

  1. temperatureat reflux for 15 hours
  2. temperaturecooled
  3. customquenched by the addition of H2O(0.88 mL), NaOH (1.5 N, 0.88 mL) and additional H2O(2.6 mL)
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e05278dedadb4e9d8943a8830d1995bf
Source dataset
uspto-grants-2002_08
Patent number
US06436954B1

Reaction notes

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