Methanol → HCID 15030108, compound

HRID 893270Notes

Reaction equation

HRID 893270 reaction equation
[N:1]1[N:2]=[N:3][N:4]2[CH:9]=[C:8]([CH:10]3[O:15][CH2:14][C:13](=O)[N:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11]3)[CH:7]=[CH:6][C:5]=12.S(C)C.CO>O1CCCC1>[N:1]1[N:2]=[N:3][N:4]2[CH:9]=[C:8]([CH:10]3[O:15][CH2:14][CH2:13][N:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11]3)[CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 15030107HCID 15030107, compound

Product 1

HCID 15030108HCID 15030108, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(tetrazolo[1,5-a]pyrid-6-yl)-4-(1,1-dimethylethyl)-5-oxo-morpholine (2.09 g) in 100 ml of dry tetrahydrofuran (THF), a 2.0M solution of BH3.Me2S in tetrahydrofuran (10 ml) was added dropwise under nitrogen. The reaction mixture was then heated at reflux for 5 hours. The mixture was cooled and treated with 25 ml of methanol. The mixture was then heated at reflux for 3 hours. The solution was concentrated under reduced pressure and the residue (2.45 g) purified by column chromatography (95:5 methylene chloride:ethanol) on silica gel to give 1.99 g of product. Mass spectrum (FAB) 262 (M+1).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 5 hours
  3. temperatureThe mixture was cooled
  4. temperatureThe mixture was then heated
  5. temperatureat reflux for 3 hours
  6. concentrationThe solution was concentrated under reduced pressure
  7. customthe residue (2.45 g) purified by column chromatography (95:5 methylene chloride:ethanol) on silica gel

Sources & evidence

ORD record
ord-9a0abe3ce4974f0b8facd8d209747c5e
Source dataset
uspto-grants-1992_06
Patent number
US05124328

Reaction notes

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