Formic Acid → HCID 18665139, compound

HRID 2393584Notes

Reaction equation

HRID 2393584 reaction equation
[NH2:1][C@H:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([O:12][CH3:13])[CH:6]=[CH:7][CH:8]=2)[CH2:3]1.[C:14](C1NC=CN=1)(C1NC=CN=1)=[O:15].C(O)=O.CO>C1COCC1.C(Cl)Cl.C(OCC)(=O)C>[CH:14]([NH:1][C@H:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([O:12][CH3:13])[CH:6]=[CH:7][CH:8]=2)[CH2:3]1)=[O:15]

Participants

8

Reactant 4

HCID 284Formic AcidHCID 887MethanolHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 9815386HCID 9815386, compound

Product 1

HCID 18665139HCID 18665139, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

As in example 6g, (-)(2S)-2-amino-8 -methoxytetralin (commercially available) (825 mg, 4.66 mmol) in 10 ml THF and 20 ml methylene chloride, was formylated with 906 mg (5.59 mmol) carbonyl diimidazole in 15 ml THF and 257 mg (5.59 mmol) formic acid in 3 ml THF. After stirring overnight, TLC analysis (silica gel; 10:90 CH3OH:CH2Cl2) indicated a major component, Rf 0.71, and absence of starting amine, Rf 0.22. The residue obtained on removal of solvent was dissolved in ethyl acetate, washed with 1N HCl, NaHCO3 solution, brine and dried (MgSO4). Filtration and removal of solvent in vacuo left a white solid, 850 mg (89%), mp 140°-141° C.

Workup

  1. customThe residue obtained on removal of solvent
  2. washwashed with 1N HCl, NaHCO3 solution, brine
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and removal of solvent in vacuo
  5. waitleft a white solid, 850 mg (89%), mp 140°-141° C.

Sources & evidence

ORD record
ord-38e653cb826c4e1787882c0f5d7e571f
Source dataset
uspto-grants-1998_09
Patent number
US05807897

Reaction notes

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