Tributylstannane → HCID 69930617, compound

HRID 518138Notes

Reaction equation

HRID 518138 reaction equation
Br[C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[O:4][CH2:5][CH:6]1[CH:10]=[CH:9][CH2:8][N:7]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C([SnH](CCCC)CCCC)CCC.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[CH2:9]1[CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]2[CH2:5][O:4][C:3]3[CH:18]=[CH:19][CH:20]=[CH:21][C:2]=3[CH:10]12

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67324400HCID 67324400, compound

Product 1

HCID 69930617HCID 69930617, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Tert-butyl 2-[(2-bromo-phenoxy)methyl]-2,5-dihydro-1H-pyrrole-1-carboxylate (14.2 g, 0.38 mol) was dissolved in toluene (707 mL) and heated at 50° C. for 20 min. To this solution was added AlBN (688 mg, 0.049 mol) and tributyltin hydride (16 mL, 0.61 mol) at room temperature. The reaction mixture was stirred at 80° C. for 16 h and then DBU (9.5 mL, 0.62 mol) was added. The resulting suspension was filtered through a pad of silica gel (100 g) and the solids washed with methyl tert-butylether. The filtrate was evaporated. The crude product was purified using an ISCO instrument (330 g RediSep® column), eluting with a gradient of ethyl acetate in heptane (from 10% ethyl acetate in 10 minutes, then 20% ethyl acetate for 15 min) to provide the title product. MS m/z 299 [M+Na]+

Workup

  1. filtrationThe resulting suspension was filtered through a pad of silica gel (100 g)
  2. washthe solids washed with methyl tert-butylether
  3. customThe filtrate was evaporated
  4. customThe crude product was purified
  5. washeluting with a gradient of ethyl acetate in heptane (from 10% ethyl acetate in 10 minutes

Sources & evidence

ORD record
ord-2ef1225b3e3545de99eccc4876e89403
Source dataset
uspto-grants-2015_08
Patent number
US09115147B2

Reaction notes

Loading…