(1S.2R)-1-Benzyloxy-2-(benzyloxymethyl)-3-cyclopentene synthesis

6synthesis methods

Product Name:(1S.2R)-1-Benzyloxy-2-(benzyloxymethyl)-3-cyclopentene
CAS Number:191480-69-0
Molecular formula:C20H22O2
Molecular Weight:294.39

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110567-21-0 Synthesis

(1S, 2R)-2-(Benzyloxymethyl)-1-hydroxy-3-cyclopentene

110567-21-0
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(1S.2R)-1-Benzyloxy-2-(benzyloxymethyl)-3-cyclopentene

191480-69-0
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Yield:191480-69-0 97.4%

Reaction Conditions:

Stage #1: (1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentenewith sodium t-butanolate in tetrahydrofuran at 20; for 0.416667 h;Inert atmosphere;
Stage #2: benzyl bromide in tetrahydrofuran at -5; for 0.583333 h;Inert atmosphere;Temperature;

Steps:

1; 3; 5 Example 5: Preparation method of compound NT01B

5.0 g of compound NT01A was dissolved in 60 mL of anhydrous THF.Under the protection of nitrogen,Add 3.46g sodium tert-butoxide,Stir at room temperature for about 25 minutes.Then, 6.10g of benzyl bromide was added dropwise to the reaction solution at -5°C,After continuing the reaction for 35 minutes,Warm up to room temperature,To the end of the reaction.Spin the reaction solution to dryness,The residue was purified by silica gel column chromatography (eluent: petroleum ether ethyl acetate = 5/1),7.03g product is obtained,The yield was 97.4%.

References:

CN113024490,2021,A Location in patent:Paragraph 0031-0033; 0037-0039; 0043-0045

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