Triethylamine → Phenylmethyl 8-azaspiro[4.5]dec-2-ene-8-carboxylate

HRID 734226Notes

Reaction equation

HRID 734226 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][CH:3]=[CH:2]1.CCN(CC)CC.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>C(Cl)Cl>[CH2:4]1[C:5]2([CH2:10][CH2:9][N:8]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:7][CH2:6]2)[CH2:1][CH:2]=[CH:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 223413358-Azaspiro[4.5]dec-2-ene

Product 1

HCID 69055893Phenylmethyl 8-azaspiro[4.5]dec-2-ene-8-carboxylateYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-azaspiro[4.5]dec-2-ene (2.74 g, 20 mmol) in Et3N (4.2 mL, 30 mmol) and DCM (100 mL) at 0° C. was added dropwise benzyl chloroformate (3.4 mL, 24 mmol). After 1 h, the solution was partitioned between H2O-DCM and the aqueous phase was extracted several times with DCM. The combined organic fractions were dried (Na2SO4), concentrated and purified via column chromatography (silica, 10% EtOAc in hexanes) yielding the title compound (3.85 g, 71%) as a yellow oil: LCMS (ES) m/e 272 (M+H)+.

Workup

  1. customthe solution was partitioned between H2O-DCM
  2. extractionthe aqueous phase was extracted several times with DCM
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography (silica, 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8cc91aab8c3c4c18a1d184ee8fc06df7
Source dataset
uspto-grants-2009_09
Patent number
US07592334B2

Reaction notes

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