tert-Butanol → HCID 86750087, compound

HRID 378567Notes

Reaction equation

HRID 378567 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH:11]([CH3:14])[CH:10](C(O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.C([N:37]([CH2:40]C)CC)C.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[CH2:1]([N:8]1[CH2:9][C@H:10]([NH:37][C:40]([O:46][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:25])[C@H:11]([CH3:14])[C:12]1=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19354246(+/-)-1-Benzyl-4-methyl-5-oxo-3-pyrrolidinecarboxylic acid

Product 1

HCID 86750087HCID 86750087, compound

Procedure

Compound (43) (3.40 g), 4.45 g of diphenylphosphorylazide, 1.9 g of triethylamine, and 50 ml of t-butyl alcohol were mixed and the mixture was heated under reflux for 12 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in chloroform. The solution was washed successively with a 10% citric acid aqueous solution, a 2% sodium hydroxide aqueous solution, and water and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography using chloroform-methanol (97.5:2.5 by volume) as an eluent to obtain 1.76 g of (±)-cis-1-benzyl-4-t-butoxycarbonylamino-3-methyl-2-oxopyrrolidine (44) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in chloroform
  5. washThe solution was washed successively with a 10% citric acid aqueous solution
  6. dry with materiala 2% sodium hydroxide aqueous solution, and water and dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6844b46404834b1095eb77f42624e507
Source dataset
uspto-grants-2000_02
Patent number
US06031102

Reaction notes

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