Tributylstannane → HCID 21366253, compound

HRID 133011Notes

Reaction equation

HRID 133011 reaction equation
[CH:1]1([CH2:4][C@H:5]([C@@H:28](OS(N2C=CN=C2)=O)[CH2:29][CH2:30][CH2:31][CH3:32])[C:6]([NH:8][C@H:9]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13]3[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=3[N:11]([CH3:26])[C:10]2=[O:27])=[O:7])[CH2:3][CH2:2]1.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[O:7]=[C:6]([NH:8][C@H:9]1[N:15]=[C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:13]2[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=2[N:11]([CH3:26])[C:10]1=[O:27])[C@@H:5]([CH2:4][CH:1]1[CH2:2][CH2:3]1)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 68661442HCID 68661442, compound

Product 1

HCID 21366253HCID 21366253, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4 (190 mg, 0.350 mmol), from step 2, in 10 mL of dry and degassed toluene was heated to reflux. A solution of tri-n-butyltin hydride (210 mg, 0.700 mmol) in 1 mL of toluene was added dropwise over 30 min. After an additional 5 h of reflux, the reaction was cooled, concentrated under reduced pressure. The crude mixture was purified by flash chromatography (elution with hexanes initially to remove tin-containing materials, then with 40% ethyl acetate-hexane) to afford 128 mg (85%) of compound 5 as a colorless gel. 1H NMR (300 MHz, CDCl3) δ 7.21-7.66 (10H, m), 5.60 (1H, d, J=8.4 Hz), 3.47 (3H, s), 2.30 (1H, m), 1.21-1.84 (10H, m), 0.91 (3H, t, J=6.2 Hz), 0.76 (1H, m), 0.46 (2H, m), 0.06 (2H, m); MS (ESI): 432 (M+H), 455 (M+Na), 430 (M−H).

Workup

  1. customdegassed toluene
  2. temperaturewas heated to reflux
  3. temperatureAfter an additional 5 h of reflux
  4. temperaturethe reaction was cooled
  5. concentrationconcentrated under reduced pressure
  6. customThe crude mixture was purified by flash chromatography (
  7. washelution with hexanes initially
  8. customto remove tin-
  9. additioncontaining materials

Sources & evidence

ORD record
ord-dad65165c3b14fc78830602504f5bade
Source dataset
uspto-grants-2008_06
Patent number
US07390802B2

Reaction notes

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