Triethylamine → (3-(4-(6-Oxa-2-azaspiro[3.4]octan-2-ylmethyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

HRID 2359371Notes

Reaction equation

HRID 2359371 reaction equation
[C:1]1([C:7]2[O:11][C:10]([C:12]([N:14]3[CH2:17][CH:16]([O:18][C:19]4[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=4)[CH2:15]3)=[O:13])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:28]1[C:31]2([CH2:35][CH2:34][O:33][CH2:32]2)[CH2:30][NH:29]1.C(N(CC)CC)C.[Na].C([O-])(O)=O.[Na+]>ClCCl>[CH2:28]1[C:31]2([CH2:35][CH2:34][O:33][CH2:32]2)[CH2:30][N:29]1[CH2:23][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH:16]2[CH2:15][N:14]([C:12]([C:10]3[O:11][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[N:8][N:9]=3)=[O:13])[CH2:17]2)=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 58043115HCID 58043115, compoundHCID 717440076-Oxa-2-azaspiro(3.4)octane hydrochloride

Product 1

HCID 71226400(3-(4-(6-Oxa-2-azaspiro[3.4]octan-2-ylmethyl)phenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-(5-phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde (70 mg, 0.20 mmol) in dichloromethane (2 mL) was added 6-oxa-2-azaspiro[3.4]octane hydrochloride (56 mg, 0.37 mmol) and triethylamine (0.100 mL, 0.72 mmol). After stirring at ambient temperature for 30 minutes, sodium triacetoxyhydroborate (95 mg, 0.45 mmol) was added. Stirring was continued at ambient temperature overnight, after which NaHCO3 (aq, sat, 5 ml) was added. The phases were separated with the aid of a phase separator. The aqueous phase was extracted twice with dichloromethane and dried using a phase separator. The combined organic phases were concentrated in vacuo to afford a colourless residue weighing 92 mg.

Workup

  1. stirringStirring
  2. waitwas continued at ambient temperature overnight
  3. customThe phases were separated with the aid of a phase separator
  4. extractionThe aqueous phase was extracted twice with dichloromethane
  5. customdried
  6. concentrationThe combined organic phases were concentrated in vacuo
  7. customto afford a colourless residue

Sources & evidence

ORD record
ord-3ed8f0a8401f4f23b0a111465b767a4b
Source dataset
uspto-grants-2014_04
Patent number
US08685958B2

Reaction notes

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