(1S,4R,5R,2'S,4'R)-(-)-spiro[1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-4,1'-3',5'-dioxa-2'-isopropyl-4'-phenyl-cyclohexane]-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(1S,4R,5R,2'S,4'R)-(-)-spiro[1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-4,1'-3',5'-dioxa-2'-isopropyl-4'-phenyl-cyclohexane]-3-carboxylic acid tert-butyl ester
CAS No.:870527-63-2
Molecular Formula:C₂₂H₃₁NO₅
Molecular Weight:389.492
Hs Code.:

Synonyms:(1S,4R,5R,2'S,4'R)-(-)-spiro[1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-4,1'-3',5'-dioxa-2'-isopropyl-4'-phenyl-cyclohexane]-3-carboxylic acid tert-butyl ester

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Chemical Property of (1S,4R,5R,2'S,4'R)-(-)-spiro[1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-4,1'-3',5'-dioxa-2'-isopropyl-4'-phenyl-cyclohexane]-3-carboxylic acid tert-butyl ester

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Technology Process of (1S,4R,5R,2'S,4'R)-(-)-spiro[1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-4,1'-3',5'-dioxa-2'-isopropyl-4'-phenyl-cyclohexane]-3-carboxylic acid tert-butyl ester

There total 13 articles about (1S,4R,5R,2'S,4'R)-(-)-spiro[1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-4,1'-3',5'-dioxa-2'-isopropyl-4'-phenyl-cyclohexane]-3-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: 90.0%

: 870527-72-3
(5R,6S,8R)-(-)-6-isopropyl-3-methyl-8-phenyl-7,9-dioxa-1-azaspiro-[4.5]dec-3-ene-1-carboxylic acid tert-butyl ester

: 870527-63-2
(1S,4R,5R,2'S,4'R)-(-)-spiro[1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-4,1'-3',5'-dioxa-2'-isopropyl-4'-phenyl-cyclohexane]-3-carboxylic acid tert-butyl ester

Guidance literature:: With 2,6-di-tert-butyl-4-methyl-phenol; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 18h;
DOI:10.1039/b508300a

Reference yield:

: 870527-57-4
(2R,3S)-(-)-2-azido-4-methyl-1-pentane-1,3-diol

: 870527-63-2
(1S,4R,5R,2'S,4'R)-(-)-spiro[1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-4,1'-3',5'-dioxa-2'-isopropyl-4'-phenyl-cyclohexane]-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 78 percent / p-toluenesulfonic acid monohydrate / toluene / 1 h / Heating

2.1: 98 percent / H₂ / Pd/CaCO₃ / ethanol / 3 h / 20 °C / 760 Torr

3.1: K₂CO₃ / acetonitrile / 0.5 h / 40 °C

3.2: acetonitrile / 18 h / Heating

4.1: 14 percent / KHMDS / diethyl ether / 0.25 h / 20 °C

5.1: 93 percent / NH₂OH*HCl; Et₃N / CH₂Cl₂ / 96 h / 20 °C

6.1: 90 percent / mCPBA; 2,6-di-tert-butyl-4-methylphenol / CH₂Cl₂ / 18 h / 20 °C

With 2,6-di-tert-butyl-4-methyl-phenol; hydroxylamine hydrochloride; hydrogen; potassium hexamethylsilazane; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In diethyl ether; ethanol; dichloromethane; toluene; acetonitrile;
DOI:10.1039/b508300a

Reference yield:

: 870527-70-1
(2R,4S,5R)-(-)-5-azido-4-isopropyl-2-phenyl[1,3]dioxane

: 870527-63-2
(1S,4R,5R,2'S,4'R)-(-)-spiro[1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-4,1'-3',5'-dioxa-2'-isopropyl-4'-phenyl-cyclohexane]-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / H₂ / Pd/CaCO₃ / ethanol / 3 h / 20 °C / 760 Torr

2.1: K₂CO₃ / acetonitrile / 0.5 h / 40 °C

2.2: acetonitrile / 18 h / Heating

3.1: 14 percent / KHMDS / diethyl ether / 0.25 h / 20 °C

4.1: 93 percent / NH₂OH*HCl; Et₃N / CH₂Cl₂ / 96 h / 20 °C

5.1: 90 percent / mCPBA; 2,6-di-tert-butyl-4-methylphenol / CH₂Cl₂ / 18 h / 20 °C

With 2,6-di-tert-butyl-4-methyl-phenol; hydroxylamine hydrochloride; hydrogen; potassium hexamethylsilazane; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In diethyl ether; ethanol; dichloromethane; acetonitrile;
DOI:10.1039/b508300a