HCID 66885344, compound → HCID 59431058, compound

HRID 2204051Notes

Reaction equation

HRID 2204051 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)[CH:12]([C:31]2[CH:36]=[CH:35][C:34](Cl)=[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)[N:11]([CH3:48])[CH:10]1[CH2:49][O:50]CC1C=CC=CC=1)C1C=CC=CC=1>CO.C(O)(=O)C.[Pd]>[CH2:46]([O:45][C:42]1[CH:43]=[CH:44][C:39]([CH2:38][C:33]2[CH:32]=[C:31]([C@H:12]3[C@H:13]([OH:23])[C@@H:14]([OH:15])[C@H:9]([OH:8])[C@@H:10]([CH2:49][OH:50])[N:11]3[CH3:48])[CH:36]=[CH:35][CH:34]=2)=[CH:40][CH:41]=1)[CH3:47]

Participants

5

Reactant 1

HCID 66885344HCID 66885344, compound

Product 1

HCID 59431058HCID 59431058, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Compound from step E (50 mg) in methanol and acetic acid (25 uL) was treated 5% wet Pd—C (10 mg) under H2 atmosphere for 4 h. The reaction mixture was filtered through a pad of celite and concentrated. Chromatography on silica gel (10 to 100% acetonitrile containing 0.1% ammonium acetate/water gradient) provided (2S,3S,4R,5R,6R)-2-[3-(4-ethoxy-benzyl)-phenyl]-6-hydroxymethyl-1-methyl-piperidine-3,4,5-triol (6 mg, 70%).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-fdb9566ed8c7439c81455ca0355847e2
Source dataset
uspto-grants-2016_06
Patent number
US09365602B2

Reaction notes

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