Potassium tert-butoxide → 6-(4-(Benzyloxy)phenyl)morpholin-3-one

HRID 920538Notes

Reaction equation

HRID 920538 reaction equation
CC([O-])(C)C.[K+].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([OH:28])[CH2:22][NH:23][C:24](=[O:27])[CH2:25]Cl)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CC(O)(CC)C.C1COCC1>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:22][NH:23][C:24](=[O:27])[CH2:25][O:28]2)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 66653971N-[2-(4-benzyloxy-phenyl)-2-hydroxy-ethyl]-2-chloro-acetamide

Product 1

HCID 666539576-(4-(Benzyloxy)phenyl)morpholin-3-oneYield 92%

Reagents, catalysts & solvents 2

HCID 64052-Methyl-2-butanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of KOtBu (6.68 g; 59.5 mmol) in 2-methyl-2-butanol (100 mL) was added dropwise a solution of N-[2-(4-benzyloxy-phenyl)-2-hydroxy-ethyl]-2-chloro-acetamide (17.30 g; 54.1 mmol) in THF (100 mL). The resulting mixture was stirred for 1 hour at RT and then concentrated in vacuo. The residue was dissolved in CH2Cl2 and treated with a 1M aqueous solution of HCl, at 0° C. The layers were separated and the aqueous layer extracted with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to afford 6-(4-benzyloxy-phenyl)-morpholin-3-one (14.10 g).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. additiontreated with a 1M aqueous solution of HCl, at 0° C
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted with CH2Cl2
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cc8dfc6382524223bbac312f627718d6
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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