(2S,5S,6R)-2-Benzyloxymethyl-6-formyl-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,5S,6R)-2-Benzyloxymethyl-6-formyl-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester
CAS No.:748781-35-3
Molecular Formula:C₂₃H₃₃NO₄
Molecular Weight:387.519
Hs Code.:

Synonyms:(2S,5S,6R)-2-Benzyloxymethyl-6-formyl-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,5S,6R)-2-Benzyloxymethyl-6-formyl-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,5S,6R)-2-Benzyloxymethyl-6-formyl-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

There total 9 articles about (2S,5S,6R)-2-Benzyloxymethyl-6-formyl-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

: 748781-31-9
(2S,5S)-5-Benzyloxymethyl-2-(2-oxo-ethyl)-2-[4-(toluene-4-sulfonyloxy)-butyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

: 748781-35-3
(2S,5S,6R)-2-Benzyloxymethyl-6-formyl-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

Guidance literature:: (2S,5S)-5-Benzyloxymethyl-2-(2-oxo-ethyl)-2-[4-(toluene-4-sulfonyloxy)-butyl]-pyrrolidine-1-carboxylic acid tert-butyl ester; With pyrrolidine; In toluene; Heating;

With acetic acid; at 20 ℃; Further stages.;
DOI:10.1016/j.tetlet.2004.05.142

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 748781-35-3
(2S,5S,6R)-2-Benzyloxymethyl-6-formyl-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / Na₂CO₃ / benzene / 20 °C

2.1: 96 percent / Bu₄NF / tetrahydrofuran / 20 °C

3.1: 93 percent / pyridine / 20 °C

4.1: 85 percent / OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 °C

5.1: pyrrolidine / toluene / Heating

5.2: 60 percent / ag. AcOH / 20 °C

With pyrrolidine; pyridine; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; sodium carbonate; In tetrahydrofuran; water; toluene; benzene;
DOI:10.1016/j.tetlet.2004.05.142

Reference yield:

: 152500-21-5
(S)-5-benzyloxymetyl-1-tert-butoxycarbonyl-2-pyrrolidinone

: 748781-35-3
(2S,5S,6R)-2-Benzyloxymethyl-6-formyl-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 85 percent / tetrahydrofuran / 0 °C

2.1: TFA / CH₂Cl₂ / 0 - 20 °C

2.2: 87 percent / NaOH / 0 °C

3.1: 79 percent / DMAP; TEA / CH₂Cl₂

4.1: 74 percent / BF₃Et₂₀ / tetrahydrofuran / -78 °C

5.1: 90 percent / Na₂CO₃ / benzene / 20 °C

6.1: 96 percent / Bu₄NF / tetrahydrofuran / 20 °C

7.1: 93 percent / pyridine / 20 °C

8.1: 85 percent / OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 °C

9.1: pyrrolidine / toluene / Heating

9.2: 60 percent / ag. AcOH / 20 °C

With pyrrolidine; pyridine; dmap; sodium periodate; osmium(VIII) oxide; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium carbonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene; benzene; 1.1: Grignard reaction / 4.1: Grignard reaction;
DOI:10.1016/j.tetlet.2004.05.142