Neopentyl alcohol → 3-(6-Hepten-1-yl)-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 366542Notes

Reaction equation

HRID 366542 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:32](O)[CH2:33][CH2:34][CH2:35][CH2:36][CH:37]=[CH2:38].C(O)C(C)(C)C.[CH:46]12[CH2:51][CH:50]1[C:49](=[O:52])[NH:48][C:47]2=[O:53]>O1CCCC1>[CH2:32]([N:48]1[C:49](=[O:52])[CH:50]2[CH:46]([CH2:51]2)[C:47]1=[O:53])[CH2:33][CH2:34][CH2:35][CH2:36][CH:37]=[CH2:38]

Participants

7

Reactant 5

HCID 6404Neopentyl alcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 543123Hept-6-en-1-olHCID 37200533-Azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 232899913-(6-Hepten-1-yl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (0.5 g) was added dropwise over 1 minute to a stirred solution of triphenylphosphine (0.75 g) in tetrahydrofuran (20 ml) at -78° C. under a nitrogen atmosphere. The reaction mixture was stirred for 5 minutes and then 6-hepten-1-ol (0.36 g) was added dropwise over 1 minute, followed by stirring at -78° C. for a further 5 minutes. Neopentanol (0.12 g) was added to the reaction mixture, followed by 3-azabicyclo[3.1.0]hexane-2,4dione (0.32 g) and stirring was continued for a further 5 minutes at -78° C. The reaction mixture was warmed to room temperature and stirred overnight. The volatiles were removed by evaporation in vacuo and the residue was triturated with hexane/dichloromethane and then filtered. The filtrate was evaporated in vacuo and then purified by chromatography on silica gel using 20% ethyl acetate/hexane as eluant. The title compound was obtained as a colourless oil (boiling point 150-160° C. @ 1 mmHg).

Workup

  1. stirringby stirring at -78° C. for a further 5 minutes
  2. stirringstirring
  3. waitwas continued for a further 5 minutes at -78° C
  4. stirringstirred overnight
  5. customThe volatiles were removed by evaporation in vacuo
  6. customthe residue was triturated with hexane/dichloromethane
  7. filtrationfiltered
  8. customThe filtrate was evaporated in vacuo
  9. custompurified by chromatography on silica gel using 20% ethyl acetate/hexane as eluant

Sources & evidence

ORD record
ord-e49494824cdf4d17ac75f706598488aa
Source dataset
uspto-grants-2000_10
Patent number
US06130241

Reaction notes

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