Tributylstannane → HCID 54320714, compound

HRID 373660Notes

Reaction equation

HRID 373660 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 69.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The resultant product from Example 124 (129 mg, 0.185 mmol) was dissolved in 10 ml dry toluene and added slowly dropwise over 30 min to a refluxing solution of tri-n-butyltin hydride (93 μl, 100 mg, 0.346 mmol) in 15 ml dry toluene under a nitrogen atmosphere. Reflux was continued for an additional 10 h. The resulting solution was cooled, concentrated in vacuo, and the residue was triturated with four 10 ml portions of acetonitrile, with gentle warming. The combined acetonitrile extracts were washed with three 20 ml portions of hexane, then the combined hexane phases were back-extracted with 20 ml of acetonitrile. All acetonitrile phases were combined and concentrated in vacuo. The crude product was purified by silica gel chromatography (hexane-ethyl acetate 9:1) to give 73 mg (69%) of the desired product. 1H NMR (CDCl3) δ 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 (bs,9H), 1.57-2.14 (several bm), 3.84 (m,1H), 3.97 (m,1H), 4.85 (dq,1H), 5.68 (d,1H), 7.3-7.46 (m,5H). Mass spectrum: (M+H)+ =571.

Workup

  1. temperatureReflux
  2. temperatureThe resulting solution was cooled
  3. concentrationconcentrated in vacuo
  4. customthe residue was triturated with four 10 ml portions of acetonitrile, with gentle warming
  5. washThe combined acetonitrile extracts were washed with three 20 ml portions of hexane
  6. extractionthe combined hexane phases were back-extracted with 20 ml of acetonitrile
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography (hexane-ethyl acetate 9:1)

Sources & evidence

ORD record
ord-fdb039fc6f2c4e9b88180c8fbe4a57b5
Source dataset
uspto-grants-1992_11
Patent number
US05164388

Reaction notes

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