Benzylamine → HCID 66954400, compound

HRID 1511803Notes

Reaction equation

HRID 1511803 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:22][CH2:21][C:18]2([O:20][CH2:19]2)[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>CO>[C:9]([O:13][C:14]([N:16]1[CH2:22][CH2:21][C:18]([CH2:19][NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([OH:20])[CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 42609244tert-Butyl 1-oxa-5-azaspiro[2.4]heptane-5-carboxylate

Product 1

HCID 66954400HCID 66954400, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzyl amine (1.7 mL, 1.1 eq) was added to a solution of rac-1-oxa-5-aza-spiro[2.4]heptane-5-carboxylic acid tert-butyl ester (commercial, 2.80 g, 14.05 mmol) in MeOH (25 mL) and the mixture was heated at reflux for 2 h. The resulting solution was concentrated under reduced pressure and the residue was purified by CC (DCM-MeOH—NH4OH 1000:50:4) to afford the title compound as colourless oil (4.29 g, 100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationThe resulting solution was concentrated under reduced pressure
  4. customthe residue was purified by CC (DCM-MeOH—NH4OH 1000:50:4)

Sources & evidence

ORD record
ord-f0666d57825f4517be5332f268d53c0c
Source dataset
uspto-grants-2012_07
Patent number
US08217029B2

Reaction notes

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