Sulfuric Acid → cis-2,6-Bis(hydroxymethyl)-4-(phenylsulfonyl)morpholine

HRID 411154Notes

Reaction equation

HRID 411154 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][N:5]([CH2:15][CH:16]1[CH2:18][O:17]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7].S(=O)(=O)(O)[OH:20].[Cl-].[Na+]>O1CCCC1>[OH:17][CH2:18][C@H:16]1[O:20][C@@H:2]([CH2:3][OH:1])[CH2:4][N:5]([S:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)(=[O:7])=[O:8])[CH2:15]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 11207928N,N-bis(2-oxiranylmethyl)benzenesulfonamide

Product 1

HCID 68460391cis-2,6-Bis(hydroxymethyl)-4-(phenylsulfonyl)morpholineYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (60 mL) was added to chirally-enriched N,N-bis(2-oxiranylmethyl)benzenesulfonamide (from step (i) above; 14.8 g, 55 mmol), followed by dilute sulfuric acid (15 mL of 1 M), and the mixture stirred for 3 days. Solid sodium chloride (11 g) was added and the mixture stirred for 1 hour. The organic phase was separated and concentrated under reduced pressure to give crude product (22.4 g). The material was purified by column chromatography over silica, eluting with dichloromethane:ethanol (19:1), to give the title compound (4 g, 25%) and an impure fraction that was a 2:1 mixture of cis- and trans-isomers (8 g, 75%).

Workup

  1. stirringthe mixture stirred for 1 hour
  2. customThe organic phase was separated
  3. concentrationconcentrated under reduced pressure
  4. customto give crude product (22.4 g)
  5. customThe material was purified by column chromatography over silica
  6. washeluting with dichloromethane:ethanol (19:1)

Sources & evidence

ORD record
ord-3a7e6b15f2f94eba9840cb566e645af7
Source dataset
uspto-grants-2003_05
Patent number
US06559143B1

Reaction notes

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