HCID 69621549, compound → HCID 69621483, compound

HRID 1826141Notes

Reaction equation

HRID 1826141 reaction equation
C([O:8][C:9]1[C:33]([O:34][CH3:35])=[CH:32][C:12]2[C:13](=[O:31])[N:14]3[CH2:30][CH2:29][CH2:28][C@H:15]3[C@H:16]([OH:27])[N:17]([C:18]([O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])=[O:19])[C:11]=2[C:10]=1[O:36][CH3:37])C1C=CC=CC=1>[Pd].CCO>[OH:8][C:9]1[C:33]([O:34][CH3:35])=[CH:32][C:12]2[C:13](=[O:31])[N:14]3[CH2:30][CH2:29][CH2:28][C@H:15]3[C@H:16]([OH:27])[N:17]([C:18]([O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:24])[CH3:25])=[O:19])[C:11]=2[C:10]=1[O:36][CH3:37]

Participants

4

Reactant 1

HCID 69621549HCID 69621549, compound

Product 1

HCID 69621483HCID 69621483, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C catalyst (0.22 g) was added to a solution of the substrate 128 (0.95 g, 2.1 mmol) in absolute EtOH (200 mL). The reaction mixture was hydrogenated under pressure using a Parr hydrogenator at 55 psi H2 for 18 h. The reaction mixture was filtered through celite, and the celite washed with hot EtOH, taking care not to allow the filtration pad to dry out. Removal of excess solvent afforded the product as a colourless glass (0.84 g, 1.9 mmol, 92%); 1H NMR (270 MHz, CDCl3) δ 0.07 (s, 9H), 0.91-0.97 (m, 2H), 2.07-2.20 (m, 4H), 3.52-3.75 (m, 2H), 3.98-4.26 (m, 9H), 5.65 (d, 1H, J=9.71 Hz), 6.26 (br s, 1H), 7.14 (s, 1H); 13C NMR (CDCl3) δ 167.0, 157.3, 146.8, 143.4, 141.3, 124.9, 123.5, 105.5, 105.2, 85.8, 64.8, 64.6, 64.5, 61.2, 60.0, 56.4, 46.4, 28.9, 28.7, 23.1, 23.0, 17.3, −1.3, −1.5, −1.7.

Workup

  1. customfor 18 h
  2. filtrationThe reaction mixture was filtered through celite
  3. washthe celite washed with hot EtOH
  4. customto dry out
  5. customRemoval of excess solvent

Sources & evidence

ORD record
ord-f47bab049d3d4b4fa3e415c3b5bb9fa2
Source dataset
uspto-grants-2006_05
Patent number
US07049311B1

Reaction notes

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