Water → HCID 66941781, compound

HRID 536674Notes

Reaction equation

HRID 536674 reaction equation
[CH2:1]([N:8]1[C:15](=[O:16])[CH2:14][CH:13]2[CH2:17][CH:9]1[CH2:10][CH2:11][C:12]2=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[CH2:20]([NH2:23])[C:21]#[CH:22]>C(O)C>[CH2:1]([N:8]1[C:15](=[O:16])[CH2:14][CH:13]2[CH2:17][CH:9]1[CH2:10][C:11]1[CH:22]=[CH:21][CH:20]=[N:23][C:12]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 239041PropargylamineHCID 66941965HCID 66941965, compound

Product 1

HCID 66941781HCID 66941781, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A flask charged with a stir bar, 2-benzyl-2-aza-bicyclo[3.3.1]nonane-3,6-dione (for preparation see J. Chem. Soc., Perkin Trans. 1, 1999, 1157-1162; 0.80 g), NaAuCl4.2 H2O (30 mg), propargylamine (0.45 mL), and ethanol (5 mL) is heated at 100° C. with microwave irradiation for 10 min. After cooling to room temperature, the mixture is filtered and the filtrate is concentrated. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate/methanol 6:4:1).

Workup

  1. additionA flask charged with a stir bar
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate is concentrated
  4. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate/methanol 6:4:1)

Sources & evidence

ORD record
ord-f74ae5d02f764f89b5467405a23f4c29
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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