HCID 52913265, compound → HCID 52913380, compound

HRID 1944099Notes

Reaction equation

HRID 1944099 reaction equation
C([O:8][C@H:9]1[C@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH3:47])=[CH:41][CH:40]=3)[CH:32]=2)[O:11][C:10]1([CH2:49][OH:50])[CH3:48])C1C=CC=CC=1>CO.Cl.[Pd]>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C@@H:12]2[O:11][C:10]([CH2:49][OH:50])([CH3:48])[C@@H:9]([OH:8])[C@H:14]([OH:15])[C@H:13]2[OH:23])=[CH:32][C:33]=1[CH2:38][C:39]1[CH:40]=[CH:41][C:42]([O:45][CH2:46][CH3:47])=[CH:43][CH:44]=1

Participants

5

Reactant 1

HCID 52913265HCID 52913265, compound

Product 1

HCID 52913380HCID 52913380, compoundYield 39.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of {(3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-methyl-tetrahydro-pyran-2-yl}-methanol (150 mg, 0.21 mmol) in methanol (10 mL) was added 10% Pd/C (70 mg) and 2 drops of conc. HCl. The reaction mixture was stirred under hydrogen atmosphere (balloon pressure) at room temperature for 18 hours. The reaction mixture was filtered through cetlie bed, washed with methanol, filtrate was concentrated and purified by preparative chiral HPLC to furnish 35 mg of (3S,4R,5R,6S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-hydroxymethyl-2-methyl-tetrahydro-pyran-3,4,5-triol.

Workup

  1. filtrationThe reaction mixture was filtered through cetlie bed
  2. washwashed with methanol, filtrate
  3. concentrationwas concentrated
  4. custompurified by preparative chiral HPLC

Sources & evidence

ORD record
ord-eab50a0cc7dd403197ab4e0b87714c85
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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