Tributylphosphine → HCID 11371308, compound

HRID 2242940Notes

Reaction equation

HRID 2242940 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. temperatureis cooled by means of an ice bath
  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-def247ece04b483a95a630fe468acfb8
Source dataset
uspto-grants-2010_03
Patent number
US07674805B2

Reaction notes

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