Diethyl Ether → HCID 57798314, compound

HRID 2100315Notes

Reaction equation

HRID 2100315 reaction equation
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][C:10](=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([C:23]#[N:24])(C)C.C(OCC)C.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>CO.[I-].[Zn+2].[I-]>[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][C:10]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)([C:23]#[N:24])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8083MorpholineHCID 82115Trimethylsilyl cyanideHCID 37355581-(Diphenylmethyl)azetidin-3-one

Product 1

HCID 57798314HCID 57798314, compound

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 887MethanolSolvent

Procedure

To a flask in an ice-bath was added 1-(diphenylmethyl)azetidin-3-one (3.0 g, 12.6 mmol), trimethylsilylcyanide (1.69 ml, 12.6 mmol) and diethyl ether (1 ml) followed by addition of zinc iodide (0.003 g). This gave a yellow suspension which turned to an orange solution after 20 mins stirring at room temperature. To the solution was added a solution of morpholine (1.1 g, 12.6 mmol) in methanol (6 ml). The solution was then refluxed overnight and no starting material remained by tlc. The reaction mixture was evaporated to dryness and the product crystallised from ethyl acetate/iso-hexane to give 1-(diphenylmethyl)-3-morpholin-4-ylazetidine-3-carbonitrile as a pale yellow crystalline solid. Analytical LCMS: single peak (214 nm), 5.74 min.

Workup

  1. customThis gave a yellow suspension which
  2. temperatureThe solution was then refluxed overnight
  3. customThe reaction mixture was evaporated to dryness
  4. customthe product crystallised from ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-df68ccb3c325469db906c6fd65f2667b
Source dataset
uspto-grants-2009_08
Patent number
US07572792B2

Reaction notes

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