1,4-Dioxane → HCID 86674831, compound

HRID 2405397Notes

Reaction equation

HRID 2405397 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13]C(C)(C)C)=O)[CH2:7]1)[CH3:2].O1CCOCC1.C(N(CC)[CH:29]([CH3:31])[CH3:30])(C)C.C1(C(Cl)=O)CC1>Cl.C(OCC)C.ClCCl>[CH:29]1([C:11]([N:8]2[CH2:9][CH2:10][C@H:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:18])[CH2:7]2)=[O:13])[CH2:31][CH2:30]1

Participants

8

Reactant 4

HCID 312751,4-DioxaneHCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 71635480HCID 71635480, compound

Product 1

HCID 86674831HCID 86674831, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

In a round bottom flask, a solution of 1,1-dimethylethyl (3R)-3-[2-(ethyloxy)-2-oxoethyl]-1-pyrrolidinecarboxylate (2.08 mmol) in 4M HCl in dioxane (10 mL, 40 mmol) was stirred at room temperature for 1 h. Analysis of an aliquot by LCMS confirmed complete removal of the BOC group from the starting material. The reaction was concentrated in vacuo to give a pale yellow liquid, which was dissolved in diethyl ether and concentrated to dryness in vacuo to yield a white solid. A solution of this intermediate as the HCl salt in dichloromethane (100 mL) was treated with N,N-diisopropylethylamine (4.16 mmol) and stirred for 5 min at room temperature. The yellow solution was treated with cyclopropanecarbonyl chloride (2.287 mmol) dropwise by syringe. The solution was allowed to warm to room temperature and stirred for 1 h. The reaction was diluted with dichloromethane (100 mL) and was washed with water, dried over magnesium sulfate, and concentrated in vacuo to give the title compound as a yellow oil (quantitative). MS(ES)+ m/e 226.1 [M+H]+.

Workup

  1. customremoval of the BOC group from the starting material
  2. concentrationThe reaction was concentrated in vacuo
  3. customto give a pale yellow liquid, which
  4. concentrationconcentrated to dryness in vacuo
  5. customto yield a white solid
  6. temperatureto warm to room temperature
  7. stirringstirred for 1 h
  8. washwas washed with water
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4637762cd7044de69795eb2a5173c854
Source dataset
uspto-grants-2014_08
Patent number
US08802864B2

Reaction notes

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