[6'-(3-Methoxyprop-1-yn-1-yl)dispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl]imidodicarbonate → Di-tert-butyl [6'-(3-methoxypropyl)dispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl]imidodicarbonate

HRID 873697Notes

Reaction equation

HRID 873697 reaction equation
[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[CH:7]=[C:8]2[C:27](=[CH:28][CH:29]=1)[O:26][CH2:25][C:21]1([CH2:24][O:23][CH2:22]1)[C:9]12[CH2:13][O:12][C:11]([N:14]([C:18]([O-:20])=[O:19])[C:15]([O-:17])=[O:16])=[N:10]1>[Pd].CCO>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:27](=[CH:28][CH:29]=1)[O:26][CH2:25][C:21]1([CH2:24][O:23][CH2:22]1)[C:9]12[CH2:13][O:12][C:11]([N:14]([C:18]([O:20][C:9]([CH3:21])([CH3:13])[CH3:8])=[O:19])[C:15]([O:17][C:6]([CH3:7])([CH3:29])[CH3:5])=[O:16])=[N:10]1

Participants

4

Reactant 1

HCID 86724226[6'-(3-Methoxyprop-1-yn-1-yl)dispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl]imidodicarbonate

Product 1

HCID 86724225Di-tert-butyl [6'-(3-methoxypropyl)dispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl]imidodicarbonateYield 199.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

[6′-(3-methoxyprop-1-yn-1-yl)dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl]imidodicarbonate (34.7 mg, 0.067 mmol) and 10% palladium on carbon (7 mg) in EtOH (1.4 mL) was stirred for 13 hours under a hydrogen atmosphere (4.5 kgf/cm2). The mixture was filtered off, and the filtrate was evaporated to give crude di-tert-butyl [6′-(3-methoxypropyl)dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl]imidodicarbonate (34.7 mg).

Workup

  1. filtrationThe mixture was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-c0ca7ec641fc48fe8a82238e7e0866ce
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

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