Tributylphosphine → HCID 11371308, compound

HRID 912740Notes

Reaction equation

HRID 912740 reaction equation
[N:1](C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[OH:19][CH2:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]([O:33]C)=O)=[O:28])[CH2:23][CH2:22]1.C(P(CCCC)CCCC)CCC.O[C:49]1[CH:58]=[C:57]2[C:52]([CH:53]=[CH:54][CH:55]=[N:56]2)=[CH:51][CH:50]=1>C1C=CC=CC=1.N.CO>[N:56]1[C:57]2[C:52](=[CH:51][CH:50]=[C:49]([O:19][CH2:20][CH:21]3[CH2:22][CH2:23][N:24]([C:27]([O:29][CH2:30][C:31]([NH2:1])=[O:33])=[O:28])[CH2:25][CH2:26]3)[CH:58]=2)[CH:53]=[CH:54][CH:55]=1

Participants

8

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 67418417HCID 67418417, compoundHCID 1354268667-Hydroxyquinoline

Product 1

HCID 11371308HCID 11371308, compoundYield 48.5%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 241BenzeneSolventHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

0.26 g (1.03 mmol) of 1,1′-(azodicarbonyl)-dipiperidine (ADDP) is added to a solution of 0.16 g (0.69 mmol) of 2-(methyloxy)-2-oxoethyl 4-(hydroxymethyl)-1-piperidinecarboxylate, prepared in Step 8.1., 0.26 ml (1.03 mmol) of tri-n-butylphosphine and 0.13 g (0.90 mmol) of 7-hydroxyquinoline in 2.5 ml of benzene, which is cooled by means of an ice bath. The mixture is stirred at 0° C. for 15 minutes and then at ambient temperature for 16 hours. It is filtered over celite and rinsed with diethyl ether. The filtrates are evaporated to dryness and purified by chromatography on silica gel, eluting with a 70/30 mixture of ethyl acetate in n-hexane. The product obtained is dissolved in 3 ml (21 mmol) of a 7M solution of ammonia in methanol. The solution is stirred for 3 hours and then evaporated to dryness. The product is purified by chromatography on silica gel, eluting with a 90/10 mixture of ethyl acetate in ethanol, and recrystallized from ethyl acetate, to give 0.115 g of product in white solid form.

Workup

  1. customprepared in Step 8.1
  2. waitat ambient temperature for 16 hours
  3. filtrationIt is filtered over celite
  4. washrinsed with diethyl ether
  5. customThe filtrates are evaporated to dryness
  6. custompurified by chromatography on silica gel
  7. washeluting with a 70/30 mixture of ethyl acetate in n-hexane
  8. customThe product obtained
  9. stirringThe solution is stirred for 3 hours
  10. customevaporated to dryness
  11. customThe product is purified by chromatography on silica gel
  12. washeluting with a 90/10 mixture of ethyl acetate in ethanol
  13. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-90f7756f39c14e658fad971a6b49cbfb
Source dataset
uspto-grants-2011_09
Patent number
US08026258B2

Reaction notes

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