4-Methylmorpholine → HCID 19385750, compound

HRID 2399433Notes

Reaction equation

HRID 2399433 reaction equation
[C:1]([C:4]1[CH2:9][C:8]([C:23]#[N:24])([C:10]2[CH:15]=[CH:14][C:13](OC)=[C:12]([O:18][CH2:19][CH:20]3[CH2:22][CH2:21]3)[CH:11]=2)[CH2:7][CH2:6][C:5]=1[O:25][CH2:26][O:27][CH3:28])([OH:3])=O.C[N:30]1CCOCC1.ClC(OCC(C)C)=O.[OH-].[NH4+]>COCCOC>[NH2:30][C:1]([C:4]1[CH2:9][C:8]([C:23]#[N:24])([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:18][CH2:19][CH:20]3[CH2:21][CH2:22]3)[CH:11]=2)[CH2:7][CH2:6][C:5]=1[O:25][CH2:26][O:27][CH3:28])=[O:3]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 62365Isobutyl chloroformateHCID 18973695HCID 18973695, compound

Product 1

HCID 19385750HCID 19385750, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-carboxy-4-cyano-4-(3-cyclopropylmethoxy-4-methoxyphenyl)-1-(methoxymethyloxy)cyclohex-1-ene (0.26 g. 0.67 mmol), N-methyl morpholine (0.09 ml, 0.8 mmol) and isobutyl chloroformate (0.1 mL, 0.77 mmol) in dry 1,2-dimethoxyethane (7 mL) was stirred under an argon atmosphere at room temperature for 10 min. Ammonium hydroxide (0.07 mL, 1.0 mmol) was added and stirring was continued for 0.5 h. The mixture was partitioned between methylene chloride and 5% aqueous sodium carbonate, was extracted three times, the organic layer was dried (potassium carbonate) and the solvent was removed in vacuo to provide a white solid (0.22 g, 85%): m.p. 120°-122° C.

Workup

  1. stirringstirring
  2. waitwas continued for 0.5 h
  3. customThe mixture was partitioned between methylene chloride and 5% aqueous sodium carbonate
  4. extractionwas extracted three times
  5. dry with materialthe organic layer was dried (potassium carbonate)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-556c818357c444ba920fe73af9e5c96d
Source dataset
uspto-grants-1995_09
Patent number
US05449686

Reaction notes

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