(2S,1'R,2'R)-2-(N-tert-butoxycarbonyl-5-methylenecyclohexyl)glycine methyl ester

Base Information

Chemical Name:(2S,1'R,2'R)-2-(N-tert-butoxycarbonyl-5-methylenecyclohexyl)glycine methyl ester
CAS No.:173027-98-0
Molecular Formula:C₁₇H₂₇NO₆
Molecular Weight:341.404
Hs Code.:

Synonyms:

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Chemical Property of (2S,1'R,2'R)-2-(N-tert-butoxycarbonyl-5-methylenecyclohexyl)glycine methyl ester

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Technology Process of (2S,1'R,2'R)-2-(N-tert-butoxycarbonyl-5-methylenecyclohexyl)glycine methyl ester

There total 11 articles about (2S,1'R,2'R)-2-(N-tert-butoxycarbonyl-5-methylenecyclohexyl)glycine methyl 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:

: 129483-65-4
(4S)-1,1-Dimethylethyl 4-<(E)-3'-methoxy-3'-oxo-1'-propenyl>-2,2-dimethyl-3-oxazolidinecarboxylate

: 173027-98-0
(2S,1'R,2'R)-2-(N-tert-butoxycarbonyl-5-methylenecyclohexyl)glycine methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: aq. NaOH / tetrahydrofuran / 18 h / 0 - 20 °C

2.1: 8.90 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / 20 °C

3.1: toluene / 75 h / 130 °C

3.2: NaOH / tetrahydrofuran; H₂O / 16 h / 0 - 20 °C

4.1: 1.00 g / methanol; diethyl ether

5.1: 72 percent / tetrahydrofuran; toluene / 2 h / -78 - 0 °C

6.1: pyridinium p-toluenesulfonate / methanol / 0.5 h / 60 °C

7.1: molecular sieves 4A; pyridinium dichromate / dimethylformamide / 15 h / 20 °C

8.1: 450 mg / methanol; diethyl ether

With dmap; sodium hydroxide; dipyridinium dichromate; 4 A molecular sieve; pyridinium p-toluenesulfonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Hydrolysis / 2.1: Esterification / 3.1: Diels-Alder reaction / 3.2: Hydrolysis / 4.1: Methylation / 5.1: Condensation / 6.1: Ring cleavage / 7.1: Oxidation / 8.1: Methylation;
DOI:10.1016/S0040-4020(98)00219-1

Reference yield:

: (S)-4-((E)-2-Carboxy-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 173027-98-0
(2S,1'R,2'R)-2-(N-tert-butoxycarbonyl-5-methylenecyclohexyl)glycine methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 8.90 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / 20 °C

2.1: toluene / 75 h / 130 °C

2.2: NaOH / tetrahydrofuran; H₂O / 16 h / 0 - 20 °C

3.1: 1.00 g / methanol; diethyl ether

4.1: 72 percent / tetrahydrofuran; toluene / 2 h / -78 - 0 °C

5.1: pyridinium p-toluenesulfonate / methanol / 0.5 h / 60 °C

6.1: molecular sieves 4A; pyridinium dichromate / dimethylformamide / 15 h / 20 °C

7.1: 450 mg / methanol; diethyl ether

With dmap; dipyridinium dichromate; 4 A molecular sieve; pyridinium p-toluenesulfonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Esterification / 2.1: Diels-Alder reaction / 2.2: Hydrolysis / 3.1: Methylation / 4.1: Condensation / 5.1: Ring cleavage / 6.1: Oxidation / 7.1: Methylation;
DOI:10.1016/S0040-4020(98)00219-1

Reference yield:

: 167281-00-7
(1'S,2E)-4-nitrophenyl 3-[5-(tert-butyl)oxycarbonyl-4,4-dimethyl-3,5-oxazolidinyl]prop-2-enoate

: 173027-98-0
(2S,1'R,2'R)-2-(N-tert-butoxycarbonyl-5-methylenecyclohexyl)glycine methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: toluene / 72 h / 130 °C

1.2: NaOH / tetrahydrofuran; H₂O / 0 - 20 °C

2.1: 1.00 g / methanol; diethyl ether

3.1: 72 percent / tetrahydrofuran; toluene / 2 h / -78 - 0 °C

4.1: pyridinium p-toluenesulfonate / methanol / 0.5 h / 60 °C

5.1: molecular sieves 4A; pyridinium dichromate / dimethylformamide / 15 h / 20 °C

6.1: 450 mg / methanol; diethyl ether

With dipyridinium dichromate; 4 A molecular sieve; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; toluene; 1.1: Diels-Alder reaction / 1.2: Hydrolysis / 2.1: Methylation / 3.1: Condensation / 4.1: Ring cleavage / 5.1: Oxidation / 6.1: Methylation;
DOI:10.1016/S0040-4020(98)00219-1