Methanol → HCID 68978453, compound

HRID 749438Notes

Reaction equation

HRID 749438 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:21][CH2:20][C:15]4([O:19][CH2:18][CH2:17][O:16]4)[CH2:14][CH2:13]3)[CH2:9]2)C=CC=CC=1.[Cl:28]C(OC(Cl)C)=O.CO>C(Cl)Cl>[ClH:28].[NH:8]1[CH2:11][CH:10]([N:12]2[CH2:13][CH2:14][C:15]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:20][CH2:21]2)[CH2:9]1

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 68978078HCID 68978078, compound

Product 1

HCID 68978453HCID 68978453, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-[1-(Diphenylmethyl)azetidin-3-yl]-1,4-dioxa-8-azaspiro[4.5]decane (0.5 g, 1.4 mmol) was dissolved in dry CH2Cl2 under nitrogen and to the resultant solution was added 1-chloroethyl chloroformate (0.45 mL, 4.1 mmol) at 0° C. The mixture was stirred for 1.5 h and then methanol was added. The solution was heated to reflux for 20 min and then the solvent was removed by evaporation. The residue was triturated with acetone and the precipitate was then recrystallised from isopropyl alcohol. There was obtained 235 mg (73%) of 8-azetidin-3-yl-1,4-dioxa-8-azaspiro[4.5]decane hydrochloride as a solid. LCMS: m/z 199 (M+1)+.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 20 min
  3. customthe solvent was removed by evaporation
  4. customThe residue was triturated with acetone
  5. customthe precipitate was then recrystallised from isopropyl alcohol

Sources & evidence

ORD record
ord-6eeb89053d574e14801b0f2e8391eabe
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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