Divinyl sulfone → HCID 58437997, compound

HRID 2092388Notes

Reaction equation

HRID 2092388 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[CH:11]([S:13]([CH:16]=[CH2:17])(=[O:15])=[O:14])=[CH2:12]>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:17][CH2:16][S:13](=[O:15])(=[O:14])[CH2:11][CH2:12]2)[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6496Divinyl sulfoneHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamine

Product 1

HCID 58437997HCID 58437997, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (S)-1-(4-bromophenyl)ethanamine (0.144 ml, 1.0 mmol) and vinylsulfonylethene (0.100 ml, 1.0 mmol) in EtOH (4.0 ml) was heated at 100° C. and stirred for 3 h. The reaction mixture was cooled to RT and evaporated to dryness. The resulting crude material was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (gradient elution, heptane AcOEt 95:5 to 4:6) to yield the title compound (256 mg, 0.804 mmol, 80% yield) as a colorless oil which crystallized on standing into a colorless solid. TLC: RF=0.40 (heptane AcOEt 1:1); HPLC: BtRet=1.29 min; LC-MS: m/z 320.2 [M+H]+; 1H NMR (400 MHz, CDCl3): 1.39 (d, J=6.8, 3H), 2.92-3.09 (m, 8H), 3.76 (q, J=6.8, 1H), 7.19-7.26 (m, 2H), 7.45-7.53 (m, 2H).

Workup

  1. customevaporated to dryness
  2. customThe resulting crude material was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (gradient elution, heptane AcOEt 95:5 to 4:6)

Sources & evidence

ORD record
ord-a50274b2698b427985a8e9eb37a0312c
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

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