Tert-butyl (s)-(2-(methoxy(methyl)amino)-2-oxo-1-phenylethyl)carbamate → (S)-tert-butyl(2-oxo-1-phenylpropyl)carbamate

HRID 588116Notes

Reaction equation

HRID 588116 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C@@H:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9](N(OC)C)=[O:10])([CH3:4])([CH3:3])[CH3:2].[CH3:22][Mg+].[Br-]>C1COCC1>[C:1]([O:5][C:6](=[O:21])[NH:7][C@@H:8]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9](=[O:10])[CH3:22])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 10968398Tert-butyl (s)-(2-(methoxy(methyl)amino)-2-oxo-1-phenylethyl)carbamateHCID 178418689HCID 178418689, compound

Product 1

HCID 90251117(S)-tert-butyl(2-oxo-1-phenylpropyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., to a solution of (S)-tert-butyl(2-(methoxy(methyl)amino)-2-oxo-1-phenylethyl)carbamate (0.9 g, 3.06 mmol) in anhydrous THF (15 mL), was added MeMgBr (3M solution in Et2O, 2.0 mL, 6.1 mmol) and resultant mixture was allowed to warm and stirred at ambient temperature. After 2 hrs, the reaction was carefully quenched with saturated aqueous NH4Cl solution (10 mL), and the organic contents were extracted with CH2Cl2 (3×25 mL). The volatiles were removed under reduced pressure to afford (S)-tert-butyl(2-oxo-1-phenylpropyl)carbamate. The compound obtained is pure and no further purification is necessary. 1H NMR (300 MHz, CDCl3) δ 7.40-7.33 (m, 5H), 5.88 (bs, 1H), 5.28 (bs, 1H), 2.08 (s, 3H), 1.41 (s, 9H).

Workup

  1. temperatureto warm
  2. customthe reaction was carefully quenched with saturated aqueous NH4Cl solution (10 mL)
  3. extractionthe organic contents were extracted with CH2Cl2 (3×25 mL)
  4. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-259ca1249f5f4c768d4f8d468bd07177
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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