1-Octyne → 3-(1-Boc-2-(s)-pyrrolidinylmethoxy)-5-octynylpyridine

Participants

Role	Name	HCID	Charge
Reactant	1-Octyne	HCID 12370	—
Reactant	(S)-2-((5-Bromopyridin-3-yloxy)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester	HCID 15480235	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Dichlorobis(triphenylphosphine)palladium	HCID 6102075	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Triethylamine	HCID 8471	—
Product	3-(1-Boc-2-(s)-pyrrolidinylmethoxy)-5-octynylpyridine	HCID 69831506	79%

Reaction Steps

To a solution of 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-bromopyridine (300 mg, 0.84 mmol) in CH2Cl2 (10 mL) and NEt3 (0.4 mL) was added bis(triphenylphosphine)palladium (II) chloride (20 mg, 0.028 mmol), copper (1) iodide (2 mg) and 1-octyne (0.25 mL. 1.7 mmol). The reaction mixture was stirred and refluxed under N2 atmosphere for two days and then cooled to room temperature. After washing with aqueous 10% NaOH (1X), the organic layer was dried (MgSO4), concentrated and chromatographed (silica gel; hexane/EtOAc, 10: 1 to 10:2) to afford an oil (255 mg, 79%): 1H NMR (CDCl3, 300 MHz) δ0.88 (t, 3H, J=2.5 Hz), 1.20-1.38 (m, 4H), 1.42 (d, 4H, J=2.5 Hz), 1.44 (s, 9H), 1.90 (m, 1H), 2.00 (m, 1H), 2.40 (t, 2H, J=7.0 Hz), 3.12 (q, 4H, J=7.5 Hz), 3.32-3.44 (m, 2H), 3.90 (br, 1H), 4.08-4.20 (m, 2H), 7.10 (s, 1H), 8.08-8.30 (m, 2H); MS (CI/NH3) m/z 387 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06127386
Source dataset	uspto-grants-2000_10
ORD ID	ord-2b758ddecb8b4fa29333010b9bbbbfd8
Source note	uspto-grants-2000_10