HCID 86621845, compound → HCID 25154352, compound

HRID 1713583Notes

Reaction equation

HRID 1713583 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]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@:10]21[C:48]1[C:43](=[CH:44][CH:45]=[C:46]([CH2:49][C:50]3[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=3)[CH:47]=1)[O:42][CH2:41][CH2:40]2)C1C=CC=CC=1>CO.[Pd]>[CH2:56]([C:53]1[CH:52]=[CH:51][C:50]([CH2:49][C:46]2[CH:47]=[C:48]3[C@:10]4([C@H:9]([OH:8])[C@@H:14]([OH:15])[C@H:13]([OH:23])[C@@H:12]([CH2:31][OH:32])[O:11]4)[CH2:40][CH2:41][O:42][C:43]3=[CH:44][CH:45]=2)=[CH:55][CH:54]=1)[CH3:57]

Participants

4

Reactant 1

HCID 86621845HCID 86621845, compound

Product 1

HCID 25154352HCID 25154352, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

(2′S,3′R,4′S,5′R,6′R)-3′,4′,5′-Tris(benzyloxy)-6′-(benzyloxymethyl)-6-(4-ethylbenzyl)-3′,4′,5′,6′-tetrahydrospiro[chroman-4,2′-pyran] (11) (13.4 mg (0.018 mmol) was dissolved in MeOH (1 mL). Pd/C (5 mg, 10% Pd/C) was added, the reaction vessel was flushed with H2, (3×, alternating with high vacuum), then stirred under an atmosphere of H2. After 3 h, additional Pd/C (5 mg) was added and the vessel flushed again with H2 (3×, alternating with high vacuum), and the reaction mixture was stirred for an additional 16 h. The crude mixture was concentrated onto celite and chromatographed over SiO2 (ISCO system, 0-20% MeOH/CH2Cl2) to provide two fractions, with 1.7 and 6.3 mg respectively. (8 mg total, >100%). The smaller fraction was of the highest purity and was submitted for biological analysis. (The second fraction had slightly dark color, indicating some Pd contamination.) For the pure fraction: 1H NMR (300 MHz, CDCl3) δ ppm: 7.22 (m, 2H), 6.99-7.11 (m, 5H), 6.77 (d, J=8.1 Hz, 1H), 4.27-4.33 (m, 1H), 4.04-4.11 (m, 1H), 3.59-3.97 (m, 6H), 2.60 (q, J=15, 7.5 Hz, 2H), 2.37-2.46 (m, 1H), 2.12 (m, 1H), 1.21 (t, J=7.5 Hz, 3H). LC/MS 98.4% (ELSD) tR=1.80 min, calcd for C23H28O6: 400.19, found 423.0 (M+Na)+.

Workup

  1. customthe reaction vessel was flushed with H2, (3×, alternating with high vacuum),
  2. additionadditional Pd/C (5 mg) was added
  3. customthe vessel flushed again with H2 (3×, alternating with high vacuum)
  4. stirringthe reaction mixture was stirred for an additional 16 h
  5. concentrationThe crude mixture was concentrated onto celite
  6. customchromatographed over SiO2 (ISCO system, 0-20% MeOH/CH2Cl2)
  7. customto provide two fractions

Sources & evidence

ORD record
ord-0d1a613e1bc84178871ccff059db2b3e
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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