Acrylonitrile → HCID 69413565, compound

HRID 1268753Notes

Reaction equation

HRID 1268753 reaction equation
[O:1]([C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][C@H:14]3[NH:26][CH2:25][CH2:24][C@:20]45[C:21]=2[C:22]=1[O:23][CH:19]4[CH:18]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH:17]=[CH:16][C@@H:15]35)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[C:35](#[N:38])[CH:36]=[CH2:37]>C(O)C>[O:1]([C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][C@H:14]3[N:26]([CH2:37][CH2:36][C:35]#[N:38])[CH2:25][CH2:24][C@:20]45[C:21]=2[C:22]=1[O:23][CH:19]4[CH:18]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:29])[CH3:30])[CH:17]=[CH:16][C@@H:15]35)[Si:2]([C:5]([CH3:7])([CH3:6])[CH3:8])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 69414903HCID 69414903, compound

Product 1

HCID 69413565HCID 69413565, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,6-Bis(t-butyldimethylsiloxy)-7,8-didehydro-4,5-epoxymorphinan (0.26 g, 0.52 mmol) was dissolved in absolute ethanol (3 mL) and acrylonitrile (0.07 ml, 1.0 mmol) was added dropwise at room temperature. The reaction mixture was stirred at room temperature overnight, and the solvent was evaporated under reduced pressure to give a white solid (0.26 g, 90% yield).

Workup

  1. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e6b88f5a97e642c28e58c4c1768de311
Source dataset
uspto-grants-2007_04
Patent number
US07199129B2

Reaction notes

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