HCID 67074229, compound → HCID 67074723, compound

HRID 1944097Notes

Reaction equation

HRID 1944097 reaction equation
C([O:8][C@@H:9]1[C@@H:16]([O:17]CC2C=CC=CC=2)[C@H:15]([O:25]CC2C=CC=CC=2)[C:12]2([CH2:14][CH2:13]2)[O:11][C@H:10]1[O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:48][O:47][C:44]1[CH:43]=[CH:42][C:41]([CH2:40][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[O:33][CH:10]2[CH:9]([OH:8])[CH:16]([OH:17])[CH:15]([OH:25])[C:12]3([CH2:14][CH2:13]3)[O:11]2)=[CH:46][CH:45]=1

Participants

4

Reactant 1

HCID 67074229HCID 67074229, compound

Product 1

HCID 67074723HCID 67074723, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (5R,6R,7S,8S)-6,7,8-tris-benzyloxy-5-[2-(4-methoxy-benzyl)-phenoxy]-4-oxa-spiro[2.5]octane (190 mg, 0.29 mmol) in methanol (5 ml) was added 10% Pd/C (60 mg) and stirred under hydrogen atmosphere at room temperature overnight. The reaction mixture was filtered through celite bed, washed with methanol (20 mL). The crude product was purified by preparative HPLC to furnish the title compound (22 mg).

Workup

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

Sources & evidence

ORD record
ord-1e274e6a48c249a68bafd3c4700fa5a5
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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