Lithium Hydroxide → HCID 24863837, compound

HRID 2427478Notes

Reaction equation

HRID 2427478 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[C:6]([Cl:20])[C:7]=1[CH2:8][N:9]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:10]1=[O:19].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.[Li+].[OH-]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH:5]=[C:6]([Cl:20])[C:7]=1[CH2:8][N:9]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:10]1=[O:19]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8083MorpholineHCID 86629430HCID 86629430, compound

Product 1

HCID 24863837HCID 24863837, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Heat a solution of trifluoro-methanesulfonic acid 3,5-dichloro-4-(1-oxo-2-aza-spiro[4.5]dec-2-ylmethyl)-phenyl ester (0.15 g, 0.32 mmol) and morpholine (0.099 g, 1.13 mmol) in 1-methyl-2-pyrrolidine (2.5 mL) to 201° C. for 1.5 hours in a microwave reactor. Cool the reaction to room temperature and treat with 2M LiOH (1 mL) and stir 16 hours at room temperature. Dilute the reaction with ethyl acetate and wash with water. Dry the organic layer with Na2SO4 and remove the solvent in vacuo to afford crude product. Purify on silica isocratically using 5% methyl t-butyl ether in chloroform to afford 0.064 g (50%) of the titled product. Rf=0.22 (9:1 chloroform:methyl t-butyl ether). MS (m/z): 397 (M+).

Workup

  1. temperatureCool
  2. customthe reaction to room temperature
  3. additionDilute
  4. washwash with water
  5. dry with materialDry the organic layer with Na2SO4
  6. customremove the solvent in vacuo
  7. customto afford crude product
  8. customPurify on silica

Sources & evidence

ORD record
ord-0ddbd0b7427f405db0d46a6622e28f7d
Source dataset
uspto-grants-2011_06
Patent number
US07968585B2

Reaction notes

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