Allyltributylstannane → HCID 54040908, compound

HRID 1379557Notes

Reaction equation

HRID 1379557 reaction equation
[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7]3[CH:15]=[CH:14][C:13](Br)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:18].[CH2:19]([Sn](CCCC)(CCCC)CC=C)[CH2:20][CH2:21]C>C(#N)C>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7]3[CH:15]=[CH:14][C:13]([CH2:21][CH:20]=[CH2:19])=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:18]

Participants

4

Reactant 2

HCID 90628AllyltributylstannaneHCID 15355317(4aR)-(10bR)-4,10b-dimethyl-8-bromo-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

Product 1

HCID 54040908HCID 54040908, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 9 g portion of (4aR)-(10bR)-4,10b-dimethyl-8-bromo-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one was combined with 11.1 g of tri-n-butyl-2-propenylstannane and 1.69 g of tetrakis(triphenylphosphene)palladium in 40 mL of acetonitrile in a sealable tube. Argon was bubbled through the mixture, the cap replaced, and the reaction heated at 90° for 18 h. Upon cooling, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was triturated with diethyl ether to obtain 4.23 g of crystalline product, and a second crop of 1.31 g of product was also obtained. mp 144°-146°. FDMS 255 M+. Calcd for C17 H21N1O2 :

Workup

  1. customArgon was bubbled through the mixture
  2. temperaturethe reaction heated at 90° for 18 h
  3. temperatureUpon cooling
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-ab8876874a624168b81c586aede6e754
Source dataset
uspto-grants-1997_09
Patent number
US05670514

Reaction notes

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