Triethylamine → (3-Hydroxyazetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

HRID 1035217Notes

Reaction equation

HRID 1035217 reaction equation
[C:1]1([C:7]2[O:11][C:10]([C:12]([O:14]CC)=O)=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-]#N.[Na+].Cl.[OH:21][CH:22]1[CH2:25][NH:24][CH2:23]1.C(N(CC)CC)C>CO.ClCCl.O>[OH:21][CH:22]1[CH2:25][N:24]([C:12]([C:10]2[O:11][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][N:9]=2)=[O:14])[CH2:23]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8929Sodium CyanideHCID 651752Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylateHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 58043098(3-Hydroxyazetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanoneYield 90%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a clear solution of ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.40 g, 1.83 mmol) in dry methanol (5 mL) was added sodium cyanide (18 mg, 0.37 mmol). A solution of 3-hydroxyazetidine hydrochloride (0.45 g, 2.84 mmol) and triethylamine (0.40 mL, 2.84 mmol) in methanol (5 mL) was added at ambient temperature. After stirring for 20 min water (20 mL) and dichloromethane (30 mL) were added. The layers were separated and the aqueous phase was extracted twice with dichloromethane (30 mL). The combined organic layers were evaporated. The crude product was then treated with toluene (5 mL), filtered, washed with toluene (5 mL) and dried in vacuo. There was obtained 0.40 g (90%) of 53A as a solid. 1H NMR (400 MHz, DMSO-d6): δ 3.84 (dd, 1H), 4.31 (m, 2H), 4.56 (m, 1H), 4.79 (dd, 1H), 5.87 (d, 1H), 7.64 (m, 3H), 8.05 (d, 2H), MS (APCI+) m/z 246 [M+H]+.

Workup

  1. additionwere added
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted twice with dichloromethane (30 mL)
  4. customThe combined organic layers were evaporated
  5. additionThe crude product was then treated with toluene (5 mL)
  6. filtrationfiltered
  7. washwashed with toluene (5 mL)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-34ae3134172e4cb4aa36bcac8e4fd2c1
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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