Tributylphosphine → HCID 67073446, compound

HRID 493988Notes

Reaction equation

HRID 493988 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].[CH2:16]([N:23]1[CH2:27][CH2:26][C@@H:25](O)[CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][C@H:25]1[CH2:26][CH2:27][N:23]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:24]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylateHCID 643472(R)-(+)-1-Benzyl-3-pyrrolidinol

Product 1

HCID 67073446HCID 67073446, compoundYield 49%

Procedure

To a cold (0° C.) mixture of ethyl-5-hydroxyindole-2-carboxylate (purchased at Biosynth, H-6350, 20.5 g, 1.0 eq.), (R)-1-benzyl-3-pyrrolidinol (23 g, 1.3 eq.) and tri-n-butylphosphine (58 mL, 2.0 eq.) was slowly added 1,1′-(azodicarbonyl)dipiperidine (50.4 g, 2.0 eq.) in several portions. The reaction mixture was stirred at room temperature overnight and then filtered off. The filtrate was concentrated in vacuo and diethylether was added. The precipitate was filtered off and the filtrate was concentrated in vacuo and purified on silica eluting with dichloromethane/methanol/ammoniac. One fraction was isolated and dried in vacuo, to yield 18 mg (49%) of the desired product as light yellow foam. MS (m/e): 365.5 (MH+, 100%).

Workup

  1. filtrationfiltered off
  2. concentrationThe filtrate was concentrated in vacuo and diethylether
  3. additionwas added
  4. filtrationThe precipitate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. custompurified on silica eluting with dichloromethane/methanol/ammoniac
  7. customOne fraction was isolated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-d024a6d5e3604913acf95ba2e7876f1d
Source dataset
uspto-grants-2009_05
Patent number
US07538101B2

Reaction notes

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