Hydrochloric Acid → HCID 52914480, compound

HRID 1944080Notes

Reaction equation

HRID 1944080 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[C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[CH:43][CH:42]=2)[CH:34]=1)C1C=CC=CC=1.Cl>CO.[Pd]>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([C@H:10]2[C@H:9]([OH:8])[C@@H:16]([OH:17])[C@H:15]([OH:25])[C:12]3([CH2:14][CH2:13]3)[O:11]2)=[CH:34][C:35]=1[CH2:40][C:41]1[CH:42]=[CH:43][C:44]([O:47][CH2:48][CH3:49])=[CH:45][CH:46]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 52914479HCID 52914479, compound

Product 1

HCID 52914480HCID 52914480, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (5S,6S,7R,8S)-6,7,8-tris-benzyloxy-5-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-4-oxa-spiro[2.5]octane (70 mg, 0.10 mmole) in methanol (3 mL), 10% Pd/C (45 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 celite bed, washed with methanol (20 mL). Crude product was purified by preparative HPLC to furnish 15 mg of the title compound.

Workup

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

Sources & evidence

ORD record
ord-d051ad713d9149bc8a374bc506ba41d1
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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