Triethylamine → 5-Chloro-2-(hexahydro-1H-7a-pyrrolizinyl)furo[3,2-b]pyridine

HRID 611577Notes

Reaction equation

HRID 611577 reaction equation
[C:1]([C:3]12[CH2:10][CH2:9][CH2:8][N:7]1[CH2:6][CH2:5][CH2:4]2)#[CH:2].[Cl:11][C:12]1[N:17]=[C:16](I)[C:15]([OH:19])=[CH:14][CH:13]=1.C(N(CC)CC)C>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:11][C:12]1[N:17]=[C:16]2[CH:2]=[C:1]([C:3]34[CH2:10][CH2:9][CH2:8][N:7]3[CH2:6][CH2:5][CH2:4]4)[O:19][C:15]2=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 195976957a-ethynylhexahydro-1H-pyrrolizineHCID 234331586-Chloro-2-iodo-3-hydroxypyridine

Product 1

HCID 195976235-Chloro-2-(hexahydro-1H-7a-pyrrolizinyl)furo[3,2-b]pyridineYield 77%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

7a-Ethynyl-hexahydro-1H-pyrrolizine from Example 15b (225 mg, 1.66 mol, 6-chloro-2-iodo-3-pyridinol (509 mg, 2.0 mmol), copper(I) iodide (60 mg, 0.30 mmol), bis(triphenylphosphine)palladium(II) chloride (58 mg, 0.08 mmol) and triethylamine (0.280 mL, 2.0 mmol) were combined in a similar fashion as that described in Example 15c. The crude product was chromatographed (silica gel; CHCl3 /MeOH, 97.5:2.5) to afford a waxy tan solid (335 mg, 77%): 1H NMR (CDCl3, 300 MHz) δ 1.88-1.97 (m, 6H), 2.21-2.33 (m, 2H), 2.67-2.79 (m, 2H), 3.19-3.26 (m, 2H), 6.70 (s, 1H), 7.14 (d, J=8.5 Hz, 1H), 7.61 (d, J=8.5 Hz, 1H); MS (CI/NH3) m/z: 263 (M+H)+.

Workup

  1. customThe crude product was chromatographed (silica gel; CHCl3 /MeOH, 97.5:2.5)

Sources & evidence

ORD record
ord-a36483df191c47929431d9e747c5ed7e
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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