HCID 18596382, compound → HCID 18661280, compound

HRID 965206Notes

Reaction equation

HRID 965206 reaction equation
Cl[C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C@H:3]1[NH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[CH2:16]([O:15][C:13]1[O:14][C@H:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][CH2:4][C@H:3]2[N:12]=1)[CH3:17]

Participants

3

Reactant 1

HCID 18596382HCID 18596382, compound

Product 1

HCID 18661280HCID 18661280, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (±) trans-1-chloro-2-ethoxycarbonylamino-1,2,3,4-tetrahydronaphthalene (L. M. Gaster and B. S. Orlek, EP 88575)(1.0 g, 4.0 mmol) in ethanol (100 ml) was treated dropwise with a solution of KHCO3 (0.44 g, 4.4 mmol in 30 ml water) over a period of 3 h. After stirring for a further 30 min the reaction was concentrated under high vacuum to approximately one quarter the original volume, then diluted with water and extracted into diethyl ether (3×100 ml). The combined extracts were washed with brine, dried over Na2SO4 and concentrated in vacua. Flash chromatography on silica gel using petroleum ether 60/80-ethyl acetate as eluant, followed by distillation in a kugelrohr (b.p. 180° C. at 0.4 mmHg) afforded the title compound as a colourless oil (0.69 g).

Workup

  1. concentrationwas concentrated under high vacuum to approximately one quarter the original volume
  2. additiondiluted with water
  3. extractionextracted into diethyl ether (3×100 ml)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacua
  7. distillationfollowed by distillation in a kugelrohr (b.p. 180° C. at 0.4 mmHg)

Sources & evidence

ORD record
ord-776dc9121a8741fb918beab09f6fd3c7
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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