Triethylamine → HCID 87243707, compound

HRID 539041Notes

Reaction equation

HRID 539041 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].CCN(CC)CC.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([O:1][CH2:2][C@@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1514267tert-Butyl (3R)-3-(hydroxymethyl)morpholine-4-carboxylate

Product 1

HCID 87243707HCID 87243707, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (R)-tert-butyl 3-(hydroxymethyl)morpholine-4-carboxylate (0.650 g, 2.99 mmol) in dichloromethane (10 mL) was added Et3N (1.25 mL, 8.98 mmol). MeSO2Cl (0.35 mL, 4.5 mmol) was added dropwise at 0° C. under N2 and the reaction mixture was stirred at 0° C. for 1 hour. The reaction was diluted with dichloromethane, washed with saturated aqueous NaHCO3 and brine, dried and concentrated. The residue was purified by silica gel chromatography (1:1 hexane/EtOAc) to give (S)-tert-butyl 3-((methylsulfonyloxy)methyl)morpholine-4-carboxylate (0.720 g, 81%) as a white solid.

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (1:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-62ce1afc1cde4168a9c450a52db9ef1a
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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