Diethyl Ether → Tert-butyl (1S)-2-morpholin-4-yl-1-phenylethylcarbamate

HRID 875142Notes

Reaction equation

HRID 875142 reaction equation
CS(O[CH2:6][C@@H:7]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=O)=O.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(OCC)C>C1COCC1>[N:22]1([CH2:6][C@@H:7]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8083MorpholineHCID 10335849(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl methanesulfonate

Product 1

HCID 57444157Tert-butyl (1S)-2-morpholin-4-yl-1-phenylethylcarbamateYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 25 g (0.0792 mol) of (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethyl methanesulfonate and morpholine (69.37 mL, 0.792 mol) in 250 mL of dry THF under inert atmosphere was refluxed for 8 hours. The reaction was then cooled to room temperature, treated with diethylether and the solid filtered. The solution was evaporated affording the crude as a yellow oil that was purified through silica gel chromatography (eluant hexane/ethylacetate 6/4). 11.59 g of the title product were isolated (48% yield).

Workup

  1. temperaturewas refluxed for 8 hours
  2. filtrationthe solid filtered
  3. customThe solution was evaporated
  4. customaffording the crude as a yellow oil that
  5. customwas purified through silica gel chromatography (eluant hexane/ethylacetate 6/4)

Sources & evidence

ORD record
ord-f4b09fabc000466db21221dafbdb9b10
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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