Azetidine → HCID 58562553, compound

HRID 1896808Notes

Reaction equation

HRID 1896808 reaction equation
[CH2:1]([O:4][CH:5]([CH:9]1[CH2:18][CH2:17][C:12]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:11][CH2:10]1)[CH2:6][CH:7]=[CH2:8])C=C.N1CCC1>C(Cl)Cl>[O:4]1[CH2:1][CH:8]=[CH:7][CH2:6][CH:5]1[CH:9]1[CH2:10][CH2:11][C:12]2([O:13][CH2:14][CH2:15][O:16]2)[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 58562838HCID 58562838, compound

Product 1

HCID 58562553HCID 58562553, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 8-(1-(allyloxy)but-3-en-1-yl)-1,4-dioxaspiro[4.5]decane (454 mg, 1.80 mmol), prepared in the previous step, and the Grubbs Generation II catalyst (76 mg, 0.09 mmol) in DCM was degassed and heated to 40° C. under argon for 4 hours. After extraction with saturated NaHCO3 solution, the organic layer was concentrated in vacuo and the residue purified by flash chromatography (silica gel, ether) to afford the product.

Workup

  1. extractionAfter extraction with saturated NaHCO3 solution
  2. concentrationthe organic layer was concentrated in vacuo
  3. customthe residue purified by flash chromatography (silica gel, ether)
  4. customto afford the product

Sources & evidence

ORD record
ord-cc93434c6f0544d195591c1aaa37b546
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

Loading…