Morpholine → HCID 69944285, compound

HRID 1978090Notes

Reaction equation

HRID 1978090 reaction equation
N1CCOCC1.C([O:10][C:11]([C@H:13]([CH2:27][CH:28]([CH3:30])[CH3:29])[C@H:14]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]([O:17][CH3:18])=[O:16])=[O:12])C=C>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:11]([C@H:13]([CH2:27][CH:28]([CH3:30])[CH3:29])[C@H:14]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]([O:17][CH3:18])=[O:16])([OH:12])=[O:10]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 69943797HCID 69943797, compound

Product 1

HCID 69944285HCID 69944285, compoundYield 121.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.39 ml of morpholine and 0.05 g of tetrakis(triphenylphosphine)palladium(0) were added to a stirred solution of 0.15 g of methyl 3(R)-(allyloxycarbonyl)-2(S)-benzyloxy-5-methylhexanoate in 5 ml of tetrahydrofuran under a nitrogen atmosphere. After stirring the mixture for 0.5 hour the solvent was evaporated. The residue was dissolved in dichloromethane and washed in succession with 2M aqueous hydrochloric acid and water. The organic phase was dried over anhydrous magnesium sulphate and the solvent was evaporated. The residue was dissolved in diethyl ether and filtered. The diethyl ether solution was evaporated to give 0.16 g of methyl 3(R)-carboxy-2(S)-benzyloxy-5-methylhexanoate in the form of a yellow oil.

Workup

  1. customwas evaporated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed in succession with 2M aqueous hydrochloric acid and water
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in diethyl ether
  7. filtrationfiltered
  8. customThe diethyl ether solution was evaporated

Sources & evidence

ORD record
ord-9a48ea7c47b84e3ebdb4d2dc61f24d4d
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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