Imidazole → methyl 2-[(1S,2R,3R,5S)-2-(3,3-ethylene dioxyoctyl)-3-(tetrahydropyranyloxy)-5-(t-butylsilyloxy)-cyclopentyl]acetate

HRID 486174Notes

Reaction equation

HRID 486174 reaction equation
[CH2:1]1[CH2:30][O:29][C:3]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])([CH2:4][CH2:5][C@H:6]2[C@H:10]([O:11][CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[CH2:9][C@H:8]([OH:18])[C@H:7]2[CH2:19][C:20]([O:22][CH3:23])=[O:21])[O:2]1.[Si:31](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])(C)C.N1C=CN=C1>CN(C=O)C>[CH2:30]1[CH2:1][O:2][C:3]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])([CH2:4][CH2:5][C@H:6]2[C@H:10]([O:11][CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[CH2:9][C@H:8]([O:18][SiH2:31][C:34]([CH3:37])([CH3:36])[CH3:35])[C@H:7]2[CH2:19][C:20]([O:22][CH3:23])=[O:21])[O:29]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 22844349HCID 22844349, compound

Product 1

HCID 123524617methyl 2-[(1S,2R,3R,5S)-2-(3,3-ethylene dioxyoctyl)-3-(tetrahydropyranyloxy)-5-(t-butylsilyloxy)-cyclopentyl]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-[(1S,2R,3R,5S)-2-(3,3-ethylenedioxyoctyl)-3-(tetrahydropyranyloxy)-5-hydroxycyclopentyl]acetate (61) in DMF (80 ml) were added t-butyldimethylsilyl chloride (2.11 g) and imidazol (0.95 g), and the resultant mixture was stirred. The crude product obtained by treating in the conventional manner was subjected to silica gel column chromatography to give the title compound (62).

Workup

  1. customThe crude product obtained
  2. additionby treating in the conventional manner

Sources & evidence

ORD record
ord-796a8e181b284486abd248bbed7b24f4
Source dataset
uspto-grants-1994_03
Patent number
US05290811

Reaction notes

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