Benzylamine → HCID 22851709, compound

HRID 55456Notes

Reaction equation

HRID 55456 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](C1C=CC(S(O[C:22]2[C:23]([O:25][C@H:26]([CH3:32])[C:27]=2[C:28]([O:30][CH3:31])=[O:29])=[O:24])(=O)=O)=CC=1)([O-])=O>C(Cl)Cl>[CH2:1]([NH:8][C:22]1[C:23]([O:25][C@H:26]([CH3:32])[C:27]=1[C:28]([O:30][CH3:31])=[O:29])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 22851705HCID 22851705, compound

Product 1

HCID 22851709HCID 22851709, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 25.5 g of benzylamine are added dropwise within a period of 1 hour to a solution of 35.7 g of (R)-2-(4-nitrobenzenesulphonyloxy)-3-methoxycarbonyl-2-penten-4-olide in 250 ml of methylene chloride. The resulting benzylamine-p-nitrobenzenesulphonic acid salt is filtered off, and the filtrate is concentrated by evaporation, filtered over silica gel with toluene, and recrystallised from ether/petroleum ether. [α]D20 =+22° (3% in CHCl3), m.p. 68°-70° C., IR (CH2Cl2) 1752, 1678, 1632 cm-1.

Workup

  1. filtrationThe resulting benzylamine-p-nitrobenzenesulphonic acid salt is filtered off
  2. concentrationthe filtrate is concentrated by evaporation
  3. filtrationfiltered over silica gel with toluene
  4. customrecrystallised from ether/petroleum ether
  5. custom[α]D20 =+22° (3% in CHCl3), m.p. 68°-70° C., IR (CH2Cl2) 1752, 1678, 1632 cm-1

Sources & evidence

ORD record
ord-9f7b13d930d8406cbb70db21fd4dac26
Source dataset
uspto-grants-1997_04
Patent number
US05625059

Reaction notes

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