Hydrochloric Acid → HCID 52914480, compound

HRID 1944093Notes

Reaction equation

HRID 1944093 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([CH3:49])[CH3:48])C1C=CC=CC=1.Cl>CO.[Pd]>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C@@H:12]2[O:11][C:10]([CH3:49])([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.[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C@H:12]2[C@H:13]([OH:23])[C@@H:14]([OH:15])[C@H:9]([OH:8])[C:10]3([CH2:49][CH2:48]3)[O:11]2)=[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

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67074567HCID 67074567, compound

Product 2

HCID 52914480HCID 52914480, compoundHCID 52914726HCID 52914726, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the above crude mixture of (3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran (˜100 mg, 0.14 mmole) in methanol (3 mL), 10% Pd/C (100 mg) and 2 drops of con. HCl added and stirred under hydrogen atmosphere at room temperature for 18 hours. The reaction mixture was filtered through cetlie bed, washed with methanol (20 mL). The crude product was purified by preparative chiral HPLC to furnish 10 mg of (3S,4R,5R,6S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,2-dimethyl-tetrahydro-pyran-3,4,5-triol (Ex. 11) and 20 mg of (5S,6R,7R,8S)-5-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-4-oxa-spiro[2.5]octane-6,7,8-triol (Ex. 2).

Workup

  1. filtrationThe reaction mixture was filtered through cetlie bed
  2. washwashed with methanol (20 mL)
  3. customThe crude product was purified by preparative chiral HPLC

Sources & evidence

ORD record
ord-6c36659de3b146d280587bbb07a559c6
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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