tert-Butanol → HCID 18541793, compound

HRID 1269764Notes

Reaction equation

HRID 1269764 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH:10](C(O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>>[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH:10]([NH:19][C:22](=[O:31])[O:45][C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6386tert-Butanol2×HCID 8471TriethylamineHCID 990241-Benzyl-5-oxo-pyrrolidine-3-carboxylic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 18541793HCID 18541793, compoundYield 51%

Procedure

In tert-butyl alcohol (6 ml) was dissolved 1-benzyl-5-oxo-3-pyrrolidinecarboxylic acid (1.00 g, 4.56 mmol), and triethylamine (0.76 ml, 5.5 mmol) was added thereto. Then, a solution of diphenylphosphoryl azide (1.38 g, 5.02 mmol) in tert-butyl alcohol (4 ml) was added thereto, and the resulting mixture was refluxed for 2 hours. After completion of the reaction, the reaction solution was concentrated and the tert-butyl alcohol was removed as an azeotrope with toluene as much as possible. The residue was purified by a silica gel chromatography (eluent: ethyl acetate/hexane) to obtain tert-butyl 1-benzyl-5-oxo-3-pyrrolidinylcarbamate (480 mg, 51%).

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was refluxed for 2 hours
  3. customAfter completion of the reaction
  4. concentrationthe reaction solution was concentrated
  5. customthe tert-butyl alcohol was removed as an azeotrope with toluene as much as possible
  6. customThe residue was purified by a silica gel chromatography (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7ac59ca6545d4a46b583110908fade41
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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