Tetrahydrofuran → HCID 86676230, compound

HRID 1426485Notes

Reaction equation

HRID 1426485 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:17][CH:18]=[CH2:19])[CH:9]([CH2:14][CH:15]=[CH2:16])[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>[OH:11][CH2:10][CH:9]([N:8]([CH2:17][CH:18]=[CH2:19])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:14][CH:15]=[CH2:16]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11108397Methyl 2-[[(1,1-dimethylethoxy)carbonyl]-2-propen-1-ylamino]-4-pentenoateHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 86676230HCID 86676230, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 9855836Potassium sodium tartarateSolvent

Procedure

To a mixture of methyl 2-[(tert-butoxycarbonyl)(prop-2-en-1-yl)amino]pent-4-enoate (5.0 g) produced above and tetrahydrofuran (100 mL) was added 1M diisobutylaluminum hydride/toluene solution (60 mL) at 0° C., and the mixture was stirred at the same temperature for 15 min. The reaction mixture was diluted with aqueous potassium sodium tartrate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (3.76 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. filtrationInsoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5958d6c9a3684e60bc90d8ddaed47bd9
Source dataset
uspto-grants-2015_01
Patent number
US08933069B2

Reaction notes

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