Tributylvinyltin → HCID 67978737, compound

HRID 1895783Notes

Reaction equation

HRID 1895783 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([Sn](CCCC)(CCCC)C=C)[CH2:19]CC>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6](=[O:17])[NH:7][C@@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:18]=[CH2:19])[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 679596071,1-Dimethylethyl N-[(1R)-1-(3-bromophenyl)ethyl]carbamate

Product 1

HCID 67978737HCID 67978737, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 15220664Palladium--triphenylphosphane (1/1)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of [(R)-1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (10.26 g, 0.0342 mol.) and tributyl(vinyl)stannane (32.5 g, 30 mL, 0.103 mol.) in toluene (175 mL) was purged with nitrogen for 30 minutes before addition of bis(triphenylphosphine palladium II chloride (2.38 g, 0.0034 mol.). The stirred mixture was heated to 60° C. for 16 hours before cooling to room temperature. The reaction mixture was filtered through hyflo-supercel then evaporated to give a dark coloured oil. The oil was purified by silica gel chromatography using iso-hexanes/ethyl acetate 19:1 to yield the title compound (6.95 g, 82%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ1.39-1.51 (m, 12H), 4.80 (br s, 2H), 5.24-5.32 (m, 1H), 5.77 (d, J=17.6 Hz, 1H), 6.73 (dd, J=17.6, 10.9 Hz, 1H), 7.18-7.36 (m, 4H).

Workup

  1. temperaturebefore cooling to room temperature
  2. filtrationThe reaction mixture was filtered through hyflo-supercel
  3. customthen evaporated
  4. customto give a dark coloured oil
  5. customThe oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-49ef744f7a674647b180c8b44411cb8f
Source dataset
uspto-grants-2013_08
Patent number
US08513184B2

Reaction notes

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