N-Benzhydryl-2,5-anhydro-2,5-imino-D-glucitol → (1S,2S,3S,4R)-1,4-bis(hydroxymethyl)-5-oxa-6-azabicyclo[2.1.1]hexane-2,3-diol

HRID 486308Notes

Reaction equation

HRID 486308 reaction equation
C([N:14]1[C@:22]2([CH2:24][OH:25])[O:23][C@:15]1([C@H:18]([C@@H:20]2[OH:21])[OH:19])[CH2:16][OH:17])(C1C=CC=CC=1)C1C=CC=CC=1.[H][H]>CO.O.[Pd].[C]>[NH:14]1[C@:22]2([CH2:24][OH:25])[O:23][C@:15]1([C@H:18]([C@@H:20]2[OH:21])[OH:19])[CH2:16][OH:17]

Participants

5

Reactant 2

HCID 131718342N-Benzhydryl-2,5-anhydro-2,5-imino-D-glucitol2×HCID 178418361HCID 178418361, compound

Product 1

HCID 68719483(1S,2S,3S,4R)-1,4-bis(hydroxymethyl)-5-oxa-6-azabicyclo[2.1.1]hexane-2,3-diolYield 91%

Reagents, catalysts & solvents 2

HCID 178526108HCID 178526108, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-benzhydryl-2,5-anhydro-2,5-imino-D-glucitol (Formula XI, R3 =Ph2CH 8.40 g, 25.5 mmol) and 0.42 g of 20% PD(OH)2 /carbon in 100 mL of MeOH was set shaking on a Parr apparatus under 60 psig of hydrogen overnight. This solution was then filtered and concentrated. Hexane (ca. 300 mi) was added, and the solvent was then removed from a white solid, which was washed with ca. 200 mL of hexane. The product was recrystallized from ETOH/CH3CN to give 3.79 g (91%) of white needles, mp 139°-142.50° C. (corrected). Both 1H and 13C NMR in D2O supported the assigned structure.

Workup

  1. filtrationThis solution was then filtered
  2. concentrationconcentrated
  3. additionHexane (ca. 300 mi) was added
  4. customthe solvent was then removed from a white solid, which
  5. washwas washed with ca. 200 mL of hexane
  6. customThe product was recrystallized from ETOH/CH3CN

Sources & evidence

ORD record
ord-b4901b82f32d4c8d807a5e2d7207533c
Source dataset
uspto-grants-1994_03
Patent number
US05290948

Reaction notes

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