HCID 18516383, compound → HCID 18516380, compound

HRID 1369925Notes

Reaction equation

HRID 1369925 reaction equation
C(OC([N:8]1[C:17]2[CH:16]=[C:15]([CH2:18][CH2:19][O:20][Si](C(C)(C)C)(C)C)[CH:14]=[CH:13][C:12]=2[CH:11]2[CH2:28][CH2:29][CH2:30][C:10]2([F:31])[C:9]1=[O:32])=O)(C)(C)C>O1CCOCC1>[F:31][C:10]12[CH2:30][CH2:29][CH2:28][CH:11]1[C:12]1[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][OH:20])=[CH:16][C:17]=1[NH:8][C:9]2=[O:32]

Participants

3

Reactant 1

HCID 18516383HCID 18516383, compound

Product 1

HCID 18516380HCID 18516380, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.77 g (1.7 mmol) of 5-tert-butyloxycarbonyl-7-[2-(tert-butyldimethylsilyloxy)ethyl]-3a-fluoro-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one is stirred in 10 ml of 4 M hydrochloric acidic dioxane for 2 hours at room temperature. The batch is concentrated by evaporation in a vacuum, the residue is taken up in ethyl acetate, washed with saturated NaHCO3, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 0.26 g of product.

Workup

  1. concentrationThe batch is concentrated by evaporation in a vacuum
  2. washwashed with saturated NaHCO3
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-c8831e4ee3bc407f804446dddb9c9c3b
Source dataset
uspto-grants-2003_06
Patent number
US06579883B1

Reaction notes

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