Acetic Anhydride → (1S,2RS,5S,6S,7R)-2-acetoxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-l-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane

HRID 1974776Notes

Reaction equation

HRID 1974776 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].O[CH:9]1[C:16](=C)C[C@H:14]2[C@@H:10]1[CH2:11][C@@H:12]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[C@H:13]2/[CH:18]=[CH:19]/[C@@H:20]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>N1C=CC=CC=1>[C:5]([O:4][CH:1]1[C:9](=[CH2:16])[CH2:10][C@H:14]2[C@@H:2]1[CH2:11][C@@H:12]([O:34][Si:35]([C:38]([CH3:40])([CH3:39])[CH3:41])([CH3:36])[CH3:37])[C@H:13]2/[CH:18]=[CH:19]/[C@@H:20]([O:26][Si:27]([C:30]([CH3:32])([CH3:31])[CH3:33])([CH3:28])[CH3:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13955240(1S,2RS,5S,6S,7R)-2-hydroxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane

Product 1

HCID 14153729(1S,2RS,5S,6S,7R)-2-acetoxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-l-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octaneYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.5 ml) and pyridine (0.5 ml) were added to 95 mg (0.187 mmole) of (1S,2RS,5S,6S,7R)-2-hydroxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane obtained in Example 3, and the mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated under reduced pressure, and then subjected to column chromatography (silica gel 20 g, hexane/ethyl acetate=19/1) to give (1S,2RS,5S,6S,7R)-2-acetoxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-l-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane (101 mg, 0.184 mmole, 98%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-527dbbd978d74627a8fc8dede937e4bb
Source dataset
uspto-grants-1994_02
Patent number
US05283349

Reaction notes

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