HCID 67560374, compound → HCID 10572110, compound

HRID 363508Notes

Reaction equation

HRID 363508 reaction equation
[OH:1][CH2:2][C@:3]1([CH:9]=[CH:10][C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:12])[O:7][C:6](=[O:8])[CH2:5][CH2:4]1.[H][H]>CCOC(C)=O.[Pd]>[OH:1][CH2:2][C@@:3]1([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:12])[O:7][C:6](=[O:8])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 67560374HCID 67560374, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10572110HCID 10572110, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3.5 (0.154 g, 0.4 mmol) in EtOAc (20 mL) was treated with 10% Pd-C (0.4 g) and hydrogenated under a hydrogen balloon for 2 h. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by flash column chromatography over silica gel with EtOAc:hexanes (2:1) as eluant to give 3.3 (0.151 g, 98%) as a white solid; mp 59° C.; [α]22D +7.90° (c 1.0, CHCl3). The IR, 1H NMR, and 13C NMR were identical to those reported for the racemate 3.2. Anal. Calcd for C22H40O5 : C, 68.71; H, 10.48. Found: C, 68.81; H, 10.45.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash column chromatography over silica gel with EtOAc:hexanes (2:1) as eluant

Sources & evidence

ORD record
ord-968ec432d01f4228a19bd411caeb3736
Source dataset
uspto-grants-1999_02
Patent number
US05874464

Reaction notes

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