Triethylamine → HCID 71227163, compound

HRID 2359372Notes

Reaction equation

HRID 2359372 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][CH2:33][O:32]2)[CH2:30][NH:29]1.C(N(CC)CC)C.[Na].C([O-])(O)=O.[Na+]>ClCCl>[CH2:30]1[C:31]2([CH2:35][CH2:34][CH2:33][O:32]2)[CH2:28][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 862803555-oxa-2-azaspiro[3.4]octane hydrochloride

Product 1

HCID 71227163HCID 71227163, compoundYield 98.5%

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 5-oxa-2-azaspiro[3.4]octane hydrochloride (80 mg, 0.53 mmol) and triethylamine (0.100 mL, 0.72 mmol). After stirring at ambient temperature for 30 minutes, sodium triacetoxyhydroborate (70 mg, 0.33 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 with the aid of a phase separator. The combined organic phases were concentrated in vacuo to afford 88 mg of a colourless residue.

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 with the aid of a phase separator
  6. concentrationThe combined organic phases were concentrated in vacuo

Sources & evidence

ORD record
ord-29159a8b01e64ee6a1cabda757346737
Source dataset
uspto-grants-2014_04
Patent number
US08685958B2

Reaction notes

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