Tributylstannane → HCID 54320714, compound

HRID 893091Notes

Reaction equation

HRID 893091 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C@H:11]([C@H:20](OS(N2C=CN=C2)=O)[C@@H:21]([CH:37]([CH3:39])[CH3:38])[C:22]([N:24]2[C@H:28]([CH3:29])[C@H:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:26][C:25]2=[O:36])=[O:23])[O:10][C:9]1([CH3:49])[CH3:48])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C@H:11]([CH2:20][C@H:21]([CH:37]([CH3:38])[CH3:39])[C:22]([N:24]2[C@H:28]([CH3:29])[C@H:27]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[O:26][C:25]2=[O:36])=[O:23])[O:10][C:9]1([CH3:48])[CH3:49])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 54166805HCID 54166805, compound

Product 1

HCID 54320714HCID 54320714, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the resultant product from Example 1E (6.50 g, 9.33 mmol) in 275 ml of dry toluene was degassed with argon for 30 min. then warmed to reflux (under argon). A solution of tri-n-butyltin hydride (5.43 g, 18.6 mmol) in 75 ml of dry, degassed toluene was added dropwise over 15 min. After an additional 2 h of reflux, the reaction was cooled, concentrated and purified by flash chromatography (5% EtOAc-hexanes) to afford 4.82 g (90%) of the title compound as a white foam. 1H NMR(CDC13) 0.90 (d, 3H), 0.92 (d, 3H), 0.9-1.1 (bm, 3H), 1.06 (d, 3H), 1.15 -1.35 (bm, 3H), 1.51 (s, 9H), 1.57-2.14 (several bm, 16H total), 3.84 (m, 1H), 3.97 (m, 1H), 4.85 (dq, 1H), b 5.68 (d, 1H), 7.3-7.46 (m, 5H). Mass spectrum: (M+H)+=571.

Workup

  1. temperaturethen warmed
  2. temperatureto reflux (under argon)
  3. customdegassed toluene
  4. additionwas added dropwise over 15 min
  5. temperatureAfter an additional 2 h of reflux
  6. temperaturethe reaction was cooled
  7. concentrationconcentrated
  8. custompurified by flash chromatography (5% EtOAc-hexanes)

Sources & evidence

ORD record
ord-6a11621fe9cf413ba925a038c0d35935
Source dataset
uspto-grants-1992_06
Patent number
US05122514

Reaction notes

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