Iodoethane → HCID 58826421, compound

HRID 2244677Notes

Reaction equation

HRID 2244677 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([OH:10])[C@@H:7]([N:11]=[N+:12]=[N-:13])[CH2:6]1)=[O:4].[CH2:14](I)[CH3:15]>C(#N)C.C1COCC1>[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([O:10][CH2:14][CH3:15])[C@@H:7]([N:11]=[N+:12]=[N-:13])[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 86611033HCID 86611033, compound

Product 1

HCID 58826421HCID 58826421, compound

Reagents, catalysts & solvents 1

HCID 22177404Acetonitrile tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of (1R,3S,4S)-3-azido-4-hydroxy-cyclopentanecarboxylic acid methyl ester (500 mg) at r.t. in acetonitrile/THF 3:1 (8 ml) under an argon atmosphere were added Ag2O (1.88 g) and ethyl iodide (2.18 ml). The black suspension was stirred for 18 h at 60° C., then cooled to r.t. The black solid was filtered off and washed with ethyl acetate. The filtrate was concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 7:3) to give (1R,3S,4S)-3-azido-4-ethoxy-cyclopentanecarboxylic acid methyl ester (474 mg) as light yellow oil. MS: 214.1 ([M+H]+).

Workup

  1. temperaturecooled to r.t
  2. filtrationThe black solid was filtered off
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 7:3)

Sources & evidence

ORD record
ord-2a4ead4b08694488be25baf820fee935
Source dataset
uspto-grants-2010_03
Patent number
US07678917B2

Reaction notes

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