HCID 87383945, compound → HCID 67395241, compound

HRID 588515Notes

Reaction equation

HRID 588515 reaction equation
[C:1]([S@@:5](/[N:7]=[CH:8]/[C:9]1[N:13]([CH3:14])[CH:12]=[C:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:10]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH3:22][Mg]Br>C(Cl)Cl>[CH3:2][C:1]([CH3:4])([S@@:5]([NH:7][C@@H:8]([C:9]1[N:13]([CH3:14])[CH:12]=[C:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:10]=1)[CH3:22])=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 87383945HCID 87383945, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67395241HCID 67395241, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (S,E)-tert-butyl 5-((tert-butylsulfinylimino)methyl)-1-methyl-1H-pyrrole-3-carboxylate (3.0 g, 10 mmol) in DCM (60 mL) was slowly added methylmagnesium bromide (13.3 mL, 3.0 M in ether) at −78° C. After stirring at −78° C. for 1 h, the solution was warmed to rt and stirred for 2 h. The reaction was quenched with sat. NH4Cl solution. After separation, the organic phase was washed with brine (5 mL), dried (Na2SO4) and concentrated. Flash column chromatography (petroleum ether: EtOAc, 10:1 to 1:1) afforded tert-butyl 5-((R)-1-((S)-1,1-dimethylethylsulfinamido)ethyl)-1-methyl-1H-pyrrole-3-carboxylate (2.2 g, 70%). 1H NMR (CDCl3, 400 MHz) δ 7.15 (s, 1H), 6.47 (s, 1H), 4.48 (m, 1H), 3.62 (s, 3H), 3.18 (m, 1H), 1.68 (d, J=6.6 Hz, 3H), 1.52 (s, 9H), 1.19 (s, 9H).

Workup

  1. customat −78° C
  2. temperaturethe solution was warmed to rt
  3. stirringstirred for 2 h
  4. customThe reaction was quenched with sat. NH4Cl solution
  5. customAfter separation
  6. washthe organic phase was washed with brine (5 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9e52d2a680c44b61be814931c74d40e0
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

Loading…