Water → HCID 87383945, compound

HRID 588514Notes

Reaction equation

HRID 588514 reaction equation
[CH:1]([C:3]1[N:7]([CH3:8])[CH:6]=[C:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:4]=1)=O.[CH3:16][C:17]([S@@:20]([NH2:22])=[O:21])([CH3:19])[CH3:18].O>C(Cl)Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:17]([S@@:20](/[N:22]=[CH:1]/[C:3]1[N:7]([CH3:8])[CH:6]=[C:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:4]=1)=[O:21])([CH3:19])([CH3:18])[CH3:16]

Participants

6

Reactant 3

HCID 962WaterHCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 86657339HCID 86657339, compound

Product 1

HCID 87383945HCID 87383945, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-formyl-1-methyl-1H-pyrrole-3-carboxylate (3.0 g, 14.5 mmol), (S)-2-methylpropane-2-sulfinamide (2.6 g, 21.8 mmol) in DCM (200 mL) was added titanium isopropoxide (24.8 g, 87 mmol). The mixture was stirred at rt for 20 h then water (30 mL) was added to quench the reaction. The solid precipitate was filtered and the filtrate was concentrated and purified by flash column chromatography (petroleum ether: EtOAc, 5:1) to give (S,E)-tert-butyl 5-((tert-butylsulfinylimino)methyl)-1-methyl-1H-pyrrole-3-carboxylate (2.9 g, 63%). 1H NMR (CDCl3, 400 MHz) δ 8.30 (s, 1H), 7.29 (s, 1H), 7.02 (s, 1H), 3.89 (s, 3H), 1.48 (s, 9H), 1.16 (s, 9H).

Workup

  1. customto quench
  2. customthe reaction
  3. filtrationThe solid precipitate was filtered
  4. concentrationthe filtrate was concentrated
  5. custompurified by flash column chromatography (petroleum ether: EtOAc, 5:1)

Sources & evidence

ORD record
ord-7c945bf2ebde44c8a26c9def7e3a0398
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

Loading…