Tributyltin Chloride → Tert-butyl 2-tributylstannanylethynylpyrrolidine-1-carboxylate

HRID 715975

Reaction equation

C([Li])CCC.[C:6]([CH:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])#[CH:7].[CH2:20]([Sn:24](Cl)([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23]>C1COCC1>[CH2:29]([Sn:24]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:25][CH2:26][CH2:27][CH3:28])[C:7]#[C:6][CH:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:30][CH2:31][CH3:32]

Participants

Conditions

Temperature: -30 °C

Procedure

n-Butyllithium (1.6M in hexanes, 12.3 mL) was added over 2 minutes to a stirred solution of tert-butyl 2-ethynylpyrrolidine-1-carboxylate (3.65 g) in anhydrous THF (80 mL) at −78° C. under nitrogen and then the mixture was allowed to warm to −30° C. over one hour. Tributyltin chloride (6.41 g) was then added dropwise at −30° C. and the mixture was allowed to warm to −10° C. and quenched by addition of saturated sodium bicarbonate solution. The layers were separated and the organic layer was dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-5% to give tert-butyl 2-tributylstannanylethynylpyrrolidine-1-carboxylate (5.54 g) as a colourless oil.

Workup

temperatureto warm to −10° C.
customquenched by addition of saturated sodium bicarbonate solution
customThe layers were separated
dry with materialthe organic layer was dried (Na2SO4)
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by chromatography on silica
washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-5%

Sources & evidence

ORD record: ord-776f43b0be0942e2b951c2f0e804c936
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187494B2

Linked notes

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