tert-Butyl [(1R)-1-{[(cyclohexylmethyl)amino]carbonyl)-3-(methylthio)propyl]carbamate → HCID 86603752, compound

HRID 226447Notes

Reaction equation

HRID 226447 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]([C@H:11]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][CH2:13]SC)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CI>[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C@@H:11]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:9]2=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 86603753tert-Butyl [(1R)-1-{[(cyclohexylmethyl)amino]carbonyl)-3-(methylthio)propyl]carbamate

Product 1

HCID 86603752HCID 86603752, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6328Methyl iodideSolvent

Procedure

tert-Butyl [(1R)-1-{[(cyclohexylmethyl)amino]carbonyl}-3-(methylthio)propyl]carbamate (5.12 g) was dissolved in methyl iodide (23 mL) and stirred at room temperature for 18 hours. The excess methyl iodide was evaporated in vacuo. The residue was dissolved in tetrahydrofuran (50 mL), added lithium bis(trimethylsilyl)amide 1.0M solution in hexane (16.3 mL) at o 0° C., and then allowed to warm to room temperature and stirred for 5 hours. The resulting mixture was poured into aqueous ammonium chloride and extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4, concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=from 80/20 (v/v) to 60/40 (v/v)) to give tert-butyl [(3R)-1-(cyclohexylmethyl)-2-oxo-3-pyrrolidinyl]carbamate (2.0 g) as a pale yellow solid.

Workup

  1. customThe excess methyl iodide was evaporated in vacuo
  2. dissolutionThe residue was dissolved in tetrahydrofuran (50 mL)
  3. additionadded lithium bis(trimethylsilyl)amide 1.0M solution in hexane (16.3 mL) at o 0° C.
  4. temperatureto warm to room temperature
  5. stirringstirred for 5 hours
  6. additionThe resulting mixture was poured into aqueous ammonium chloride
  7. extractionextracted with ethyl acetate
  8. washThe organic phase was washed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=from 80/20 (v/v) to 60/40 (v/v))

Sources & evidence

ORD record
ord-31f85a958ed54774892c27d62f7afdd8
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

Loading…