Sodium Carbonate → HCID 57470864, compound

HRID 1712642Notes

Reaction equation

HRID 1712642 reaction equation
Cl.[NH:2]1[CH2:5][CH2:4][CH2:3]1.[CH:6]([N:19]1[CH2:22][C:21](=O)[CH2:20]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.C(OCC)(=O)C.O>[N:2]1([CH:21]2[CH2:22][N:19]([CH:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:20]2)[CH2:5][CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 5049666Sodium triacetoxyborohydrideHCID 12308726Azetidine hydrochloride

Product 1

HCID 57470864HCID 57470864, compoundYield 73.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Azetidine hydrochloride (326 mg) was added to a solution of 1-benzhydrylazetidin-3-one (750 mg) in dichloromethane (12 ml), followed by stirring at room temperature. Sodium triacetoxyborohydride (1.01 g) was added thereto, followed by stirring at room temperature for 25 hours. Sodium carbonate (until bubbling stopped), water (50 ml) and ethyl acetate (100 ml) was added to the reaction mixture. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The dried organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; heptane:ethyl acetate=1:1, 1:2, then ethyl acetate) to give the title compound (643 mg, 73.1%) as a pale yellow solid.

Workup

  1. stirringby stirring at room temperature for 25 hours
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe dried organic layer was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent

Sources & evidence

ORD record
ord-e1d0c00c2cbc4a64b9d6dba696693c61
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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