Tributylstannane → HCID 54320714, compound

HRID 1646908Notes

Reaction equation

HRID 1646908 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(CDCl3) 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), 5.68 (d, 1 H), 7.3-7.46 (m, 5H). Mass spectrum: (M+H)+=571.

Workup

  1. temperaturewarmed
  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-b28b9a62b75c4c97852770ccd2559b09
Source dataset
uspto-grants-1993_01
Patent number
US05182266

Reaction notes

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