tert-Butyl bromoacetate → HCID 58280086, compound

HRID 2189034Notes

Reaction equation

HRID 2189034 reaction equation
[C@H:1]1([OH:8])[CH2:6][CH2:5][CH2:4][C@H:3]([OH:7])[CH2:2]1.[C:9]([O:13][C:14](=[O:17])[CH2:15]Br)([CH3:12])([CH3:11])[CH3:10]>C1COCC1.ClCCl>[C:9]([O:13][C:14](=[O:17])[CH2:15][O:7][C@H:3]1[CH2:4][CH2:5][CH2:6][C@@H:1]([OH:8])[CH2:2]1)([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 6432541HCID 6432541, compound

Product 1

HCID 58280086HCID 58280086, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Dissolve 5.0 g (43 mmol) of cis/trans-1,3-cyclohexanediol (approx. 1.2:1 cis/trans mixture) in 20 ml of absolute THF and, at RT, add 24.8 ml (approx. 49.5 mmol) of phosphazene base P2-t-Bu in THF (approx. 2 M solution) dropwise. Stir the solution at RT for a further 30 min and then add dropwise to a mixture of 9.5 ml (64.6 mmol) of bromoacetic acid tert-butyl ester and add 10 ml of THF dropwise. Stir the mixture at RT overnight, then dilute with dichloromethane, and wash the organic phase successively with 1N hydrochloric acid, buffer solution (pH 7) and sodium chloride solution, dry over sodium sulphate and concentrate under reduced pressure. Separate the crude product by means of chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1→1:1). 2.73 g (27.6% of theory) of the cis-configured target compound are isolated as a pure fraction.

Workup

  1. stirringStir the mixture at RT overnight
  2. washwash the organic phase successively with 1N hydrochloric acid, buffer solution (pH 7) and sodium chloride solution
  3. dry with materialdry over sodium sulphate
  4. concentrationconcentrate under reduced pressure
  5. customSeparate the crude product by means of chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1→1:1)
  6. custom2.73 g (27.6% of theory) of the cis-configured target compound are isolated as a pure fraction

Sources & evidence

ORD record
ord-97a70ecfc51842bf89cc098d85df5eff
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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