1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22135434, compound

HRID 991786Notes

Reaction equation

HRID 991786 reaction equation
[N:1]12CCCN=[C:7]1CCCC[CH2:2]2.S(C[N+]#[C-])(C1C=CC(C)=CC=1)(=O)=O.[O:25]1[CH2:30][CH2:29][CH:28]=[CH:27][C:26]1=[O:31]>O1CCCC1>[CH:2]1[NH:1][CH:7]=[C:27]2[C:26](=[O:31])[O:25][CH2:30][CH2:29][C:28]=12

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 161915Tosylmethyl isocyanideHCID 5206603393-45-1

Product 1

HCID 22135434HCID 22135434, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU, 8.39 mL, 56.1 mmol) was added to a stirred mixture of tosylmethyl isocyanide (10.95 g, 56.1 mmol) in tetrahydrofuran (THF, 56 mL) at 0° C. After 15 minutes, to the mixture was added 5,6-dihydro-2H-pyran-2-one (5 g, 51 mmol). The mixture was then stirred at room temperature for 2 hours. The reaction was quenched with brine and extracted with THF several times. The combined extracts were dried (sodium sulfate), filter and concentrated to give 6,7-dihydro-2H-pyrano[3,4-c]pyrrol-4-one.

Workup

  1. customThe reaction was quenched with brine
  2. extractionextracted with THF several times
  3. dry with materialThe combined extracts were dried (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-362100eaf49e467a91ec79a8f146618b
Source dataset
uspto-grants-2002_10
Patent number
US06465507B2

Reaction notes

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