Hydrochloric Acid → HCID 86629210, compound

HRID 2384926Notes

Reaction equation

HRID 2384926 reaction equation
[OH:1][CH2:2][C@H:3]1[N:8]([CH3:9])[C:7](=[O:10])[CH2:6][O:5][CH2:4]1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.Cl>N1C=CC=CC=1>[CH3:9][N:8]1[C:7](=[O:10])[CH2:6][O:5][CH2:4][C@H:3]1[CH2:2][O:1][S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 68949899(R)-5-(hydroxymethyl)-4-methylmorpholin-3-one

Product 1

HCID 86629210HCID 86629210, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dissolve (R)-5-hydroxymethyl-4-methyl-morpholin-3-one (767 mg, 5.29 mmol) in pyridine (18 mL). Cool the reaction to 0° C., add 1.3 g (6.9 mmol) of p-toluenesulfonyl chloride (1.3 g, 6.9 mmol), and stir for 90 min. Pour into 1N HCl (50 mL) and extract with EtOAc (2×100 mL). Wash the combined organic layers with brine (50 mL), dry over Na2SO4, and concentrate to give the crude product. Purify via silica gel chromatography using a 0-100% EtOAc/hexanes gradient to yield 684 mg (43%) of the title compound. MS/ES m/z 300.0 [M+H]+.

Workup

  1. temperatureCool
  2. customthe reaction to 0° C.
  3. extractionextract with EtOAc (2×100 mL)
  4. washWash the combined organic layers with brine (50 mL)
  5. dry with materialdry over Na2SO4
  6. concentrationconcentrate
  7. customto give the crude product
  8. customPurify via silica gel chromatography

Sources & evidence

ORD record
ord-a2129889dc0b494cac6c4ba0edbff028
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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