Tributylstannane → HCID 86701263, compound

HRID 2276064Notes

Reaction equation

HRID 2276064 reaction equation
[C:1]([O:6][C@@H:7]1[C@@H:15]([CH2:16]Br)[C:14](=[O:18])[O:13][CH2:12][C@H:11]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:10](=[O:27])[O:9][C@H:8]1[CH3:28])(=[O:5])[CH:2]([CH3:4])[CH3:3].CCCC[SnH](CCCC)CCCC>C1C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C>[C:1]([O:6][C@@H:7]1[C@@H:15]([CH3:16])[C:14](=[O:18])[O:13][CH2:12][C@H:11]([NH:19][C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[C:10](=[O:27])[O:9][C@H:8]1[CH3:28])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 5948TributylstannaneHCID 86701264HCID 86701264, compound

Product 1

HCID 86701263HCID 86701263, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 241BenzeneSolvent

Procedure

To a solution of (3S,6S,7R,8R)-8-(bromomethyl)-3-(tert-butoxycarbonylamino)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (238 mg, 0.51 mmol) in benzene (3 mL) was added Bu3SnH (178 mg, 0.61 mmol) and AIBN (2 mg) at room temperature (about 22° C.). The reaction solution was heated to reflux, stirred for 1 hr, and the solution was cooled to room temperature. The solvent was removed under vacuum and the residue was purified via column chromatography (SiO2, hexanes/EtOAc gradient) to afford the title compound (185 mg, 94%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 5.40-5.12 (m, 2H), 5.00 (t, J=9.8 Hz, 1H), 4.93-4.71 (m, 2H), 3.69-3.47 (m, 1H), 2.69-2.50 (m, 2H), 1.45 (s, J=4.7 Hz, 9H), 1.28 (d, J=6.3 Hz, 3H), 1.21 (dd, J=7.0, 1.2 Hz, 6H), 1.13 (d, J=6.7 Hz, 3H); ESIMS m/z 410 ([M+Na]+).

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified via column chromatography (SiO2, hexanes/EtOAc gradient)

Sources & evidence

ORD record
ord-836a117e4d0a4eca80561eb5ab1da518
Source dataset
uspto-grants-2015_09
Patent number
US09131690B2

Reaction notes

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