Di-tert-butyl [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 594843Notes

Reaction equation

HRID 594843 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[O:17][CH2:18][C:19]2([N:37]=1)[C:28]1([CH2:31][O:30][CH2:29]1)[CH2:27][O:26][C:25]1[C:20]2=[CH:21][C:22]([C:32]#[C:33][CH2:34][O:35][CH3:36])=[CH:23][CH:24]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CCO>[CH3:36][O:35][CH2:34][CH2:33][CH2:32][C:22]1[CH:21]=[C:20]2[C:25](=[CH:24][CH:23]=1)[O:26][CH2:27][C:28]1([CH2:31][O:30][CH2:29]1)[C:19]12[CH2:18][O:17][C:16]([N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[N:37]1

Participants

4

Reactant 1

HCID 86724253Di-tert-butyl [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 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of di-tert-butyl[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-f74b704473414cf2a9ac478408a6ae88
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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