5-Iodo-1-oxo-2,3,7,8,10,11-hexahydro-1H-4-oxa-9-aza-cyclohepta[a]naphthalene-9-carboxylic acid ethyl ester → 1-Ethyl-1-hydroxy-5-iodo-2,3,7,8,10,11-hexahydro-1H-4-oxa-9-aza-cyclohepta[a]naphthalene-9-carboxylic acid ethyl ester

HRID 925235Notes

Reaction equation

HRID 925235 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:22][CH2:21][C:10]2[C:11]3[C:12](=[O:20])[CH2:13][CH2:14][O:15][C:16]=3[C:17]([I:19])=[CH:18][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:23]([Mg]Br)[CH3:24]>C(OCC)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:22][CH2:21][C:10]2[C:11]3[C:12]([CH2:23][CH3:24])([OH:20])[CH2:13][CH2:14][O:15][C:16]=3[C:17]([I:19])=[CH:18][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 867253415-Iodo-1-oxo-2,3,7,8,10,11-hexahydro-1H-4-oxa-9-aza-cyclohepta[a]naphthalene-9-carboxylic acid ethyl esterHCID 178418443HCID 178418443, compound

Product 1

HCID 867253421-Ethyl-1-hydroxy-5-iodo-2,3,7,8,10,11-hexahydro-1H-4-oxa-9-aza-cyclohepta[a]naphthalene-9-carboxylic acid ethyl esterYield 108.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into a glass vial containing the product from step (f) (170 mg, 0.409 mmol) dissolved in diethyl ether (4 ml), ethylmagnesium bromide (3M diethyl ether, 1.3 ml, 4.09 mmol) was added at reflux. The reaction mixture was stirred at reflux for 20 minutes. The reaction mixture was allowed to cool to room temperature and was then quenched with saturated aqueous NH4Cl (30 ml). The aqueous mixture was extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give a yellow oil (197 mg) that was used without further purification. MS: ESI (positive): 446 (M+H).

Workup

  1. temperatureat reflux
  2. temperatureat reflux for 20 minutes
  3. customwas then quenched with saturated aqueous NH4Cl (30 ml)
  4. extractionThe aqueous mixture was extracted with EtOAc (3×)
  5. washThe combined EtOAc extracts were washed with brine
  6. dry with materialdried over Na2SO4, and solvent
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-c7f50084ef0d470abd196e73c4c713e2
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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