HCID 57856997, compound → HCID 57857061, compound

HRID 561758Notes

Reaction equation

HRID 561758 reaction equation
[S:1]1[C:5]([C@H:6]([O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)/[CH:7]=[CH:8]/[C@@H:9]2[C@@H:16]3[C@@H:12]([O:13][CH:14]([OH:17])[CH2:15]3)[CH2:11][C@H:10]2[OH:18])=[CH:4][C:3]2[CH:37]=[CH:38][CH:39]=[CH:40][C:2]1=2.[H][H]>C(OCC)(=O)C.[Pd]>[S:1]1[C:5]([C@H:6]([O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:7][CH2:8][C@@H:9]2[C@@H:16]3[C@@H:12]([O:13][CH:14]([OH:17])[CH2:15]3)[CH2:11][C@H:10]2[OH:18])=[CH:4][C:3]2[CH:37]=[CH:38][CH:39]=[CH:40][C:2]1=2

Participants

5

Reactant 2

HCID 57856997HCID 57856997, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57857061HCID 57857061, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(3aR,4R,5R,6aS)-4-((R,E)-3-(Benzo[b]thiophen-2-yl)-3-(tert-butyldiphenylsilyloxy)prop-1-enyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol (Example 2, Step E, 1 mol equivalent) is dissolved in ethyl acetate (0.05 M) under a nitrogen atmosphere. 10% Pd/C (10 mol %) is added and hydrogen gas is introduced. After stirring for several hours at room temperature the reaction mixture is filtered over Celite. The crude product is purified by flash chromatography on regular silica gel eluted with ethyl acetate-hexanes (+0.4% acetic acid) to afford the title intermediate.

Workup

  1. filtrationis filtered over Celite
  2. customThe crude product is purified by flash chromatography on regular silica gel
  3. washeluted with ethyl acetate-hexanes (+0.4% acetic acid)

Sources & evidence

ORD record
ord-bd8cb665f8a848d8bb430acfad442663
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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