(7S,9S)-(-)-7-(4-benzyloxybutyl)-9-methyl-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(7S,9S)-(-)-7-(4-benzyloxybutyl)-9-methyl-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylic acid tert-butyl ester
CAS No.:1590401-05-0
Molecular Formula:C₂₄H₃₇NO₅
Molecular Weight:419.561
Hs Code.:

Synonyms:(7S,9S)-(-)-7-(4-benzyloxybutyl)-9-methyl-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylic acid tert-butyl ester

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Chemical Property of (7S,9S)-(-)-7-(4-benzyloxybutyl)-9-methyl-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylic acid tert-butyl ester

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Technology Process of (7S,9S)-(-)-7-(4-benzyloxybutyl)-9-methyl-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylic acid tert-butyl ester

There total 8 articles about (7S,9S)-(-)-7-(4-benzyloxybutyl)-9-methyl-1,4-dioxa-8-azaspiro[4.5]decane-8-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:

: 4541-14-4
4-benzyloxy-butan-1-ol

: 1590401-05-0
(7S,9S)-(-)-7-(4-benzyloxybutyl)-9-methyl-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-imidazole; triphenylphosphine; iodine / dichloromethane / 0.83 h / 0 - 20 °C

2.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether; cyclohexane / 3 h / -80 - -65 °C / Inert atmosphere

2.2: 2 h / -80 - -60 °C / Inert atmosphere

2.3: 12 h / -80 - 20 °C / Inert atmosphere

With 1H-imidazole; N,N,N,N,-tetramethylethylenediamine; iodine; sec.-butyllithium; triphenylphosphine; In diethyl ether; dichloromethane; cyclohexane;
DOI:10.1021/jo500104c

Reference yield:

: 50873-94-4
(4-iodobutoxymethyl)benzene

: 1590401-03-8
(7S)-(+)-7-methyl-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylic acid tert-butyl ester

: 1590401-05-0
(7S,9S)-(-)-7-(4-benzyloxybutyl)-9-methyl-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylic acid tert-butyl ester

Guidance literature:: (7S)-(+)-7-methyl-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylic acid tert-butyl ester; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; cyclohexane; at -80 - -65 ℃; for 3h; Inert atmosphere;

With copper(I) cyanide lithium chloride; In tetrahydrofuran; diethyl ether; cyclohexane; at -80 - -60 ℃; for 2h; Inert atmosphere;

(4-iodobutoxymethyl)benzene; In tetrahydrofuran; diethyl ether; cyclohexane; at -80 - 20 ℃; for 12h; Inert atmosphere;
DOI:10.1021/jo500104c

Reference yield:

: 1590400-95-5
(11S,7S)-(+)-7-methyl-8-(1-phenylethyl)-1,4-dioxa-8-azaspiro[4.5]decane-7-carbonitrile

: 1590401-05-0
(7S,9S)-(-)-7-(4-benzyloxybutyl)-9-methyl-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate / ethanol / 6 h / 0 - 20 °C

2.1: 20% palladium hydroxide-activated charcoal; hydrogen / methanol / 72 h / 20 °C / 3750.38 Torr

3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / Reflux

4.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether; cyclohexane / 3 h / -80 - -65 °C / Inert atmosphere

4.2: 2 h / -80 - -60 °C / Inert atmosphere

4.3: 12 h / -80 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; 20% palladium hydroxide-activated charcoal; hydrogen; sec.-butyllithium; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; ethanol; cyclohexane; acetonitrile;
DOI:10.1021/jo500104c