Water → 4-Tert-butyl 2-methyl 2-(tosyloxymethyl)morpholine-2,4-dicarboxylate

HRID 513107Notes

Reaction equation

HRID 513107 reaction equation
[OH:1][CH2:2][C:3]1([C:16]([O:18][CH3:19])=[O:17])[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:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.O>N1C=CC=CC=1>[S:26]([O:1][CH2:2][C:3]1([C:16]([O:18][CH3:19])=[O:17])[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])[CH2:4]1)([C:23]1[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 672284574-Tert-butyl 2-methyl 2-(hydroxymethyl)morpholine-2,4-dicarboxylate

Product 1

HCID 866714174-Tert-butyl 2-methyl 2-(tosyloxymethyl)morpholine-2,4-dicarboxylateYield 80.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

E3 (3.2 g, 11.62 mmol) was dissolved in pyridine (75 mL), p-toluenesulfonyl chloride (2.66 g, 13.95 mmol) was added in 4 portions in ca. 10 minutes and the solution was stirred for 15 h at RT. The reaction mixture was poured into water and extracted twice with EtOAc. The organic layer was washed with 1 N HCl and brine, dried over MgSO4, filtered and concentrated in vacuo. The crude was purified by flash column chromatography (heptane:EtOAc 100:0 to 40:60) yielding the title compound (4.0 g, 80%). MS (ES) C19H27NO8S requires: 429. found: 452.1 [M+Na]+.

Workup

  1. extractionextracted twice with EtOAc
  2. washThe organic layer was washed with 1 N HCl and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by flash column chromatography (heptane:EtOAc 100:0 to 40:60)

Sources & evidence

ORD record
ord-5d92ed2043fd4460908b32905f1408d1
Source dataset
uspto-grants-2015_08
Patent number
US09102676B2

Reaction notes

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