Indene oxide → HCID 68925009, compound

HRID 2375250Notes

Reaction equation

HRID 2375250 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH:14]12[O:23][CH:15]1[CH2:16][C:17]1[C:22]2=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[OH:23][C@@H:15]1[CH2:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:14]1[N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 92838Indene oxideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 68925009HCID 68925009, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

11.6 g of tert-butyl piperazine-1-carboxylate (62 mmol) and 8.2 g of indene oxide (62 mmol) are dissolved in 30 ml of acetonitrile. The reaction mixture is then heated at 60° C. overnight and evaporated to dryness. The residue obtained is purified by flash chromatography on 1 kg of silica (eluant: dichloromethane/ethanol 95/5) to yield tert-butyl trans-4-(2-hydroxy-2,3-dihydro-1H-inden-1-yl)piperazine-1-carboxylate in the form of a white meringue.

Workup

  1. customevaporated to dryness
  2. customThe residue obtained
  3. customis purified by flash chromatography on 1 kg of silica (eluant: dichloromethane/ethanol 95/5)

Sources & evidence

ORD record
ord-52957625eea74321b99cdf6798ad5c75
Source dataset
uspto-grants-2008_12
Patent number
US07465733B2

Reaction notes

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