Formic Acid → HCID 46201936, compound

HRID 1944101Notes

Reaction equation

HRID 1944101 reaction equation
C([O:8][C@@H:9]1[C@@H:17]([O:18]CC2C=CC=CC=2)[C@H:16]([O:26]CC2C=CC=CC=2)[C:12]2([CH2:15][O:14][CH2:13]2)[O:11][C@H:10]1[C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([CH2:41][C:42]2[CH:47]=[CH:46][C:45]([O:48][CH2:49][CH3:50])=[CH:44][CH:43]=2)[CH:35]=1)C1C=CC=CC=1.C(O)=O>C1COCC1.CCO.[Pd]>[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([C@H:10]2[C@H:9]([OH:8])[C@@H:17]([OH:18])[C@H:16]([OH:26])[C:12]3([CH2:13][O:14][CH2:15]3)[O:11]2)=[CH:35][C:36]=1[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][CH2:49][CH3:50])=[CH:44][CH:43]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 52913384HCID 52913384, compound

Product 1

HCID 46201936HCID 46201936, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of (6S,7S,8R,9S)-7,8,9-tris-benzyloxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,5-dioxa-spiro[3.5]nonane (110 mg, 0.15 mmol) in THF:EtOH (1:1, 5 mL) was added 10% Pd/C (60 mg) followed by formic acid (0.46 mL, 12 mmol) and stirred under hydrogen atmosphere at room temperature for 8 hours. The reaction mixture was filtered through cetlie bed, neutralized with saturated aqueous NaHCO3 solution, extracted with EtOAc, concentrated and purified by preparative HPLC to furnish 31 mg of (6S,7R,8R,9S)-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2,5-dioxa-spiro[3.5]nonane-7,8,9-triol.

Workup

  1. filtrationThe reaction mixture was filtered through cetlie bed
  2. extractionextracted with EtOAc
  3. concentrationconcentrated
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-02ff67df63c548d680f1b91e5f4a7b1f
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

Loading…