HCID 14153976, compound → HCID 14153977, compound

HRID 980816Notes

Reaction equation

HRID 980816 reaction equation
[CH2:1]([C:4]1([C:19]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=O)[C:7]2=[CH:8][C:9]([O:12][CH2:13][CH2:14][CH2:15][N:16]=[N+]=[N-])=[CH:10][CH:11]=[C:6]2[CH2:5]1)[CH:2]=[CH2:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([C:4]1([CH2:19][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:7]2=[CH:8][C:9]([O:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:10][CH:11]=[C:6]2[CH2:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 14153976HCID 14153976, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14153977HCID 14153977, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-allyl-5-(3-azidopropoxy)1-(1-piperidinylcarbonyl)benzocyclobutene (19.5 g) in THF (200 ml) is added dropwise to a stirred suspension of LAH (5.26 g) in THF (82 ml) under nitrogen. The reaction mixture is refluxed for one hour, quenched with water, 15% aqueous NaOH and water, filtered and evaporated in vacuo affording an oil which is chromatographed (silica gel: 5% triethylamine/methanol) affording the desired product as an oil.

Workup

  1. temperatureThe reaction mixture is refluxed for one hour
  2. customquenched with water, 15% aqueous NaOH and water
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customaffording an oil which
  6. customis chromatographed (silica gel: 5% triethylamine/methanol)

Sources & evidence

ORD record
ord-f2411c254d364fa19a239e6d9660eadd
Source dataset
uspto-grants-1987_01
Patent number
US04639442

Reaction notes

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