HCID 68687618, compound → HCID 68685046, compound

HRID 2245352Notes

Reaction equation

HRID 2245352 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]([NH:12]C(OC(C)(C)C)=O)[CH2:10][CH2:9][N:8]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=2)[CH2:7]1)=[O:5])[CH3:2]>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]([NH2:12])[CH2:10][CH2:9][N:8]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 68687618HCID 68687618, compound

Product 1

HCID 68685046HCID 68685046, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (3R,4R) and (3S,4S)-4-tert-butoxycarbonylamino-1-[2-(3,4-dimethoxy-phenyl)-ethyl]-piperidine-3-carboxylic acid ethyl ester (24 mg) in 1 ml TFA was stirred 1 h at 0° C. The mixture was poured onto NaOH 1M/ice and extracted with AcOEt. The combined organic layers were washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure gave an oil which was purified by column chromatography (Isolute SPE Flash NH2 10 g, AcOEt/heptane, 1/2) to give 9 mg (50%) of the title compound.

Workup

  1. additionThe mixture was poured onto NaOH 1M/ice
  2. extractionextracted with AcOEt
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent under reduced pressure
  6. customgave an oil which
  7. customwas purified by column chromatography (Isolute SPE Flash NH2 10 g, AcOEt/heptane, 1/2)

Sources & evidence

ORD record
ord-e674c0110aa3416b94a85c5a46cf56b3
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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