Pyridine → HCID 73052642, compound

HRID 1503080Notes

Reaction equation

HRID 1503080 reaction equation
[CH2:1]1[C:3]2([CH2:8][C:7](=[O:9])[O:6][C:5](=[O:10])[CH2:4]2)[CH2:2]1.Cl.[CH3:12][NH:13][O:14][CH3:15].N1C=CC=CC=1>ClCCl>[CH3:15][O:14][N:13]([CH3:12])[C:7]([CH2:8][C:3]1([CH2:4][C:5]([OH:6])=[O:10])[CH2:2][CH2:1]1)=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 54153109144728-22-3

Product 1

HCID 73052642HCID 73052642, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5 g 6-oxa-spiro[2.5]octane-5,7-dione (36 mmole), 3.8 g of N,O-dimethylhydroxylamine hydrochloride (39 mmole, 1.1 eq) and 75 ml of dichloromethane are added 7 ml of pyridine (78 mmole, 2.2 eq) at 0-5° C. The solution is warmed to room temperature, stirred over night and washed with 50 ml of brine. The aqueous phase is extracted with 3×30 ml of dichloromethane and the combined organic phases are dried over magnesium sulfate and evaporated to dryness. The resulting crude product is directly used in the next step ([1-(2-oxo-propyl)-cyclopropyl]-acetic acid).

Workup

  1. washwashed with 50 ml of brine
  2. extractionThe aqueous phase is extracted with 3×30 ml of dichloromethane
  3. dry with materialthe combined organic phases are dried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-611eb58d4fee4042adb7a8a10b8350e2
Source dataset
uspto-grants-2015_12
Patent number
US09212120B2

Reaction notes

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