Triethylamine → HCID 86659198, compound

HRID 2367595Notes

Reaction equation

HRID 2367595 reaction equation
[CH3:1][C@H:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][C@@H:5]([CH2:15][OH:16])[O:4][CH2:3]1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[CH3:24][S:25]([O:16][CH2:15][C@H:5]1[O:4][CH2:3][C@@H:2]([CH3:1])[N:7]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:6]1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 51357957HCID 51357957, compound

Product 1

HCID 86659198HCID 86659198, compoundYield 118.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of [(2S,5R)-5-methyl-4-(phenylmethyl)-2-morpholinyl]methanol (5 g, 22.59 mmol) and triethylamine (9.45 mL, 67.8 mmol) in CH2Cl2 (50 mL) stirred under nitrogen at 0° C. was added a solution of methanesulfonyl chloride (4.37 mL, 56.5 mmol) in CH2Cl2 (15 mL) dropwise during 5 minutes. The reaction mixture was stirred at 25° C. for 2.5 hours. Then the reaction mixture was washed with saturated NaHCO3 aqueous solution (2×25 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title compound (8.0 g) as a yellow oil. LC-MS (ES) m/z=300 [M+H]+.

Workup

  1. washThen the reaction mixture was washed with saturated NaHCO3 aqueous solution (2×25 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-613e3657cb67445a843d196a2adece7c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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