Methanol → Trans-1,2,3,5,6,10b-Hexahydro-6-[4'-(3-hydroxy-1(Z)-propenyl)phenyl]pyrrolo[2,1-a]isoquinoline

HRID 1275488Notes

Reaction equation

HRID 1275488 reaction equation
[OH:1][CH2:2][CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C@H:14]3[CH2:21][CH2:22][CH2:23][N:13]3[CH2:12]2)=[CH:7][CH:6]=1.N1C2C(=CC=CC=2)C=CC=1.CO.CCN(CC)CC>C(O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(Cl)Cl>[OH:1][CH2:2]/[CH:3]=[CH:4]\[C:5]1[CH:6]=[CH:7][C:8]([C@H:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C@H:14]3[CH2:21][CH2:22][CH2:23][N:13]3[CH2:12]2)=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 7047QuinolineHCID 8471TriethylamineHCID 54066242Trans-1,2,3,5,6,10b-Hexahydro-6-[4'-(3-hydroxy-1-propenyl)phenyl]pyrrolo[2,1-a]isoquinoline

Product 1

HCID 70295281Trans-1,2,3,5,6,10b-Hexahydro-6-[4'-(3-hydroxy-1(Z)-propenyl)phenyl]pyrrolo[2,1-a]isoquinolineYield 63.3%

Reagents, catalysts & solvents 3

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of trans-1,2,3,5,6,10b-Hexahydro-6-[4'-(3-hydroxy-1-propynyl)phenyl]pyrrolo[2,1-a]isoquinoline (17) (154 mg, 0.507 mmol) in 10 mL of absolute ethanol was added the Lindlar catalyst (15 mg) at room temperature followed by addition of 7 mg of quinoline. The reaction mixture was stirred under hydrogen at room temperature for 12 h, filtered through a sintered glass funnel with celite, rinsed with methylene chloride (2×10 mL). The filtrate was concentrated to afford a crude product. Flash chromatography with 3.75% MeOH, 0.075% Et3N in methylene chloride gave 98 mg of thick red oil (63% yield). 1H NMR (CDCl3) δ 1.73-2.05 (m, 3H, C2H2 & C1H), 2.30-2.2.44 (m, 1H, C1H), 2.579 (dt, 1H, J=9.0, 8.7 Hz, C3H), 2.869 (dd, 1H, J=5.1, 11.1 Hz, C5H), 2.90-3.03 (m, 2H, C3H & C5H), 3.480 (dd, 1H, J=7.2, 9.0 Hz, C10bH), 4.125 (t, 1H, J=4.8 Hz, C6H), 6.865 (d, 1H, J=7.5 Hz, aryl), 6.995 (d, 2H, J=8.1 Hz, C6 phenyl aryl), 7.04-7.20 (m, 3H, aryl), 7.575 (d, 2H, J=8.1 Hz, C6 phenyl aryl); 13C NMR (CDCl3) δ 22.17 (C2), 30.31 (C1), 45.48 (C3), 54.13 (C10b), 55.95 (C6), 63.67 (C5), 91.60 (4'C), 125.73 (aromatic), 126.30, 129.30, 130.97, 137.23.

Workup

  1. filtrationfiltered through a sintered glass funnel with celite
  2. washrinsed with methylene chloride (2×10 mL)
  3. concentrationThe filtrate was concentrated
  4. customto afford a crude product

Sources & evidence

ORD record
ord-3ed7b3588fe4425e8ad4d6ca7b347600
Source dataset
uspto-grants-2000_12
Patent number
US06162417

Reaction notes

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