Water → HCID 67325721, compound

HRID 1029038Notes

Reaction equation

HRID 1029038 reaction equation
[CH3:1][C:2](C)([O-:4])C.[K+].[Br:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[NH:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18].ClCC(OCC)=O.O>C1COCC1.CCOC(C)=O>[Br:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[N:15]1[CH2:16][C:17]([CH3:20])([CH3:18])[O:19][CH2:1][C:2]1=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 7751Ethyl chloroacetate2×HCID 23665647Potassium tert-butoxide2×HCID 67326141HCID 67326141, compound

Product 1

HCID 67325721HCID 67325721, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of potassium tert-butoxide (472 mg, 4.21 mmol) in THF (4 mL) was added a solution of 1-(2-bromo-3-methylphenylamino)-2-methylpropan-2-ol (724 mg, 2.80 mmol) in THF (10 mL), followed by ethyl 2-chloroacetate (0.45 mL, 4.21 mmol). After 1 h at RT an additional 1 eq of potassium t-butoxide (472 mg, 4.21 mmol) and ethyl 2-chloroacetate (0.450 mL, 4.21 mmol) were added. After 6 h water was added, followed by EtOAc. The organic phase was separated, dried over MgSO4 and the solvent was removed under reduced pressure. The remaining residue was purified by flash chromatography (30-80% EtOAc/hexanes). 4-(2-Bromo-3-methylphenyl)-6,6-dimethylmorpholin-3-one was isolated as a light-yellow solid.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over MgSO4
  3. customthe solvent was removed under reduced pressure
  4. customThe remaining residue was purified by flash chromatography (30-80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0d68d9a11b3748e39e09610759a2b97b
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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