tert-Butyl N-allyl-N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamate → tert-Butyl N-allyl-N-[2-oxo-2-(2-thienyl)ethyl]carbamate

HRID 470207Notes

Reaction equation

HRID 470207 reaction equation
[CH2:1]([N:4]([CH2:12][C:13](N(OC)C)=[O:14])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3].[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[Li]>O1CCCC1>[CH2:1]([N:4]([CH2:12][C:13](=[O:14])[C:20]1[S:19][CH:23]=[CH:22][CH:21]=1)[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 86697892tert-Butyl N-allyl-N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamateHCID 178418439HCID 178418439, compound

Product 1

HCID 86697895tert-Butyl N-allyl-N-[2-oxo-2-(2-thienyl)ethyl]carbamateYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl N-allyl-N-[2-(methoxy(methyl)amino)-2-oxo-ethyl]carbamate (25 g, 96.8 mmol) in tetrahydrofuran (339 mL) at −78° C. is added drop wise 2-thienyllithium (145 ml, 1 M in tetrahydrofuran) over 20 min. The reaction is carefully quenched with aqueous ammonium chloride (20 mL), diluted with water (100 mL), and extracted with dichloromethane. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated to give a residue. The residue is purified by silica gel flash chromatography, eluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (5:1) to give the title compound (15.2 g, 56%). ES/MS (m/e): 182 (M+H-100).

Workup

  1. customThe reaction is carefully quenched with aqueous ammonium chloride (20 mL)
  2. additiondiluted with water (100 mL)
  3. extractionextracted with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue
  8. customThe residue is purified by silica gel flash chromatography
  9. washeluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-ecd3dce53d7d4a58802a8e266dbecc81
Source dataset
uspto-grants-2014_01
Patent number
US08629270B2

Reaction notes

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