Tetrahydrofuran toluene → HCID 59606021, compound

HRID 1945529Notes

Reaction equation

HRID 1945529 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:14]2([CH2:17][C:16](=[O:18])[CH2:15]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][Mg]Br.C1(C)C=CC=CC=1.C1COCC1>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][C:14]2([CH2:17][C:16]([OH:18])([CH3:21])[CH2:15]2)[CH2:19][CH2:20]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 22635083Tetrahydrofuran tolueneHCID 57348595Benzyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 59606021HCID 59606021, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-oxo-7-azaspiro[3.5]nonane-7-carboxylic acid benzyl ester (164 mg, 0.60 mmol) in dry THF (2 mL) was added dropwise a 1.4 M solution of methylmagnesium bromide in toluene/THF (0.56 mL, 0.78 mmol) under an atmosphere of nitrogen, at −78° C. After 1 h the solution was quenched with saturated NH4Cl(aq) and the resulting mixture partitioned between EtOAc and water. The organic layer was dried (Na2SO4) and evaporated to give a residue, which was purified by column chromatography (Si—PCC, 0-70% EtOAc in cyclohexane) to give 2-Hydroxy-2-methyl-7-azaspiro[3.5]nonane-7-carboxylic acid benzyl ester (96 mg, 55%) as a colourless oil. LCMS (Method H): RT 4.13 min, [M+H]+ 290.4

Workup

  1. customat −78° C
  2. customAfter 1 h the solution was quenched with saturated NH4Cl(aq)
  3. customthe resulting mixture partitioned between EtOAc and water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated
  6. customto give a residue, which
  7. customwas purified by column chromatography (Si—PCC, 0-70% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-57a78bb6db164da387273fcb70883662
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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