Tributylstannane → Tert-butyl 1-(6-(tributylstannyl)pyrazin-2-yl)piperidin-3-ylcarbamate
Reaction equation
[CH2:1]([SnH:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[Li+].CC([N-]C(C)C)C.Cl[C:23]1[N:28]=[C:27]([N:29]2[CH2:34][CH2:33][CH2:32][CH:31]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:30]2)[CH:26]=[N:25][CH:24]=1>C1COCC1>[CH2:10]([Sn:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])[C:23]1[N:28]=[C:27]([N:29]2[CH2:34][CH2:33][CH2:32][CH:31]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:40])([CH3:39])[CH3:41])[CH2:30]2)[CH:26]=[N:25][CH:24]=1)[CH2:11][CH2:12][CH3:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of tri-n-butyltin hydride (1.686 mL, 6.39 mmol) in THF (10 mL) at 0° C. was added LDA (1.8 M solution in heptane/THF/ethylbenzene, 3.55 mL, 6.39 mmol) dropwise. The reaction mixture was stirred at 0° C. for 15 min and tert-butyl 1-(6-chloropyrazin-2-yl)piperidin-3-ylcarbamate (1.00 g, 3.20 mmol) was added. The reaction mixture was kept at 0° C. for 2 h, then quenched with 10% KF solution. The mixture was extracted with DCM and the combined organic layers were dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 10-25% EtOAc in Hexanes) to give tert-butyl 1-(6-(tributylstannyl)pyrazin-2-yl)piperidin-3-ylcarbamate (400 mg, 22.1% yield). MS (ESI, pos. ion) m/z: 569 (M+1).
Workup
- waitThe reaction mixture was kept at 0° C. for 2 h
- customquenched with 10% KF solution
- extractionThe mixture was extracted with DCM
- customthe combined organic layers were dried
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified with silica gel chromatography (eluting with 10-25% EtOAc in Hexanes)
Sources & evidence
- ORD record
- ord-20a7c9d95b444bf0a782843d59e0ac6e
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090593B2
Reaction notes
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