Diisopropylethylamine → 1,1-Dimethylethyl 2-[[(methylsulfonyl)oxy]methyl]-2-(hydroxymethyl)-4-morpholinecarboxylate

HRID 2110803Notes

Reaction equation

HRID 2110803 reaction equation
[OH:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.C(N(C(C)C)C(C)C)C.[CH3:25][S:26]([O:29]S(C)(=O)=O)(=O)=[O:27].[C:34]([O-])(O)=[O:35].[Na+]>ClCCl>[CH3:25][S:26]([O:1][CH2:2][C:3]1([CH2:34][OH:35])[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)(=[O:29])=[O:27]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 5201202tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylate

Product 1

HCID 866286481,1-Dimethylethyl 2-[[(methylsulfonyl)oxy]methyl]-2-(hydroxymethyl)-4-morpholinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S) 1,1-dimethylethyl 2-(hydroxymethyl)-4-morpholinecarboxylate (5.63 g) (Heterocycles, 1993, 35, 105) and N-ethyl-N,N-diisopropylamine (9 ml) in dichloromethane (200 ml) at room temperature was added methanesulfonic anhydride (5.42 g). The reaction was stirred for 16 hours. The reaction mixture was poured onto saturated aqueous NaHCO3 solution and the organics were extracted with dichloromethane. The combined organic extracts were dried with MgSO4 and concentrated to give an oil (8.33 g). This was used without further purification.

Workup

  1. extractionthe organics were extracted with dichloromethane
  2. dry with materialThe combined organic extracts were dried with MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-832497995f604c21b3b3cc20dc7cf4d4
Source dataset
uspto-grants-2009_04
Patent number
US07517989B2

Reaction notes

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