HCID 22145829, compound → HCID 22145811, compound

HRID 1994353Notes

Reaction equation

HRID 1994353 reaction equation
C([O:8][C:9]1[C:10]([O:36][CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)=[CH:11][C:12]([CH2:15][O:16][C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:13][CH:14]=1)C1C=CC=CC=1>[Pd].C(O)C>[CH:37]1([O:36][C:10]2[C:9]([OH:8])=[CH:14][N:13]=[C:12]([CH2:15][O:16][C:17]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:11]=2)[CH2:38][CH2:39][CH2:40][CH2:41]1

Participants

4

Reactant 1

HCID 22145829HCID 22145829, compound

Product 1

HCID 22145811HCID 22145811, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5% Palladium on charcoal catalyst (2 g) is added to a solution of 5-benzyloxy-4-cyclopentyloxy-2-trityloxymethylpyridine (24.2 g) in ethanol (500 mL) and the mixture stirred at room temperature under a hydrogen atmosphere for 3 hours. After filtering the filtrate is concentrated in vacuo to give a colourless oil which is purified by flash chromatography (n-pentane/ethyl acetate 7:3 v/v as eluent on silica) to give 4-cyclopentyloxy-5-hydroxy-2-trityloxymethylpyridine (18.8 g) as a colourless foam. [1Hnmr in deuterochloroform with Me4Si as standard:— 1.70, 2H, m; 1.82, 2H, m; 1.90-2.08, 4H, m; 4.25, 2H, s; 4.93, 1H, m; 7.19, 1H, s; 7.24, 7.30, 7.49, 15H, Ar; 8.04, 1H, s.].

Workup

  1. filtrationAfter filtering the filtrate
  2. concentrationis concentrated in vacuo
  3. customto give a colourless oil which
  4. customis purified by flash chromatography (n-pentane/ethyl acetate 7:3 v/v as eluent on silica)

Sources & evidence

ORD record
ord-7b74f8507c1749b9a66e7225952d7771
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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