Azetidine → HCID 58562496, compound

HRID 1896845Notes

Reaction equation

HRID 1896845 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]([OH:15])[CH2:12][CH:13]=[CH2:14])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.N1CC[CH2:17]1>C(Cl)Cl>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3([OH:15])[CH2:17][CH:14]=[CH:13][CH2:12]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 58562619HCID 58562619, compound

Product 1

HCID 58562496HCID 58562496, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 1-(1,4-dioxaspiro[4.5]decan-8-yl)but-3-en-1-ol (840 mg, 3.33 mmol), prepared in the previous step, and the Grubbs Generation II catalyst (185 mg, 0.218 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-88e7bb952119400ba7e116151ac7baaf
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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