Technology Process of 1-Piperidinecarboxylic acid,
3-(hydroxymethyl)-5-[(2R)-1,2,3,6-tetrahydro-6-oxo-2-pyridinyl]-,
phenylmethyl ester, (3S,5R)-
There total 8 articles about 1-Piperidinecarboxylic acid,
3-(hydroxymethyl)-5-[(2R)-1,2,3,6-tetrahydro-6-oxo-2-pyridinyl]-,
phenylmethyl ester, (3S,5R)- 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:
-
-
667940-07-0
(2R,3'R,5'S)-(+)-5-acetoxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester
-
-
667940-12-7
(2R,3'R,5'S)-(+)-5-hydroxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester
- Guidance literature:
-
With
sodium hydroxide;
In
tetrahydrofuran;
at 20 ℃;
for 2h;
DOI:10.1021/ol0361507
-
-
667940-12-7
(2R,3'R,5'S)-(+)-5-hydroxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: (-)-B-methoxydiisopinocampheylborane / diethyl ether / 1.25 h / -78 - 20 °C
1.2: diethyl ether / -78 - 20 °C / Acid hydrolysis
1.3: 76 percent / aq. NaOH; aq. H2O2 / 3 h / Heating
2.1: 99 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C
3.1: 87 percent / NaN3 / dimethylformamide / 2 h / 80 °C
4.1: Ph3P / tetrahydrofuran
4.2: 66 percent / H2O
5.1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C
6.1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating
7.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C
With
(-)-B-methoxydiisopinocamphenylborane; dmap; sodium hydroxide; sodium azide; triethylamine; triphenylphosphine;
Grubbs catalyst first generation;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0361507
-
-
667940-12-7
(2R,3'R,5'S)-(+)-5-hydroxymethyl-6-oxo-1,2,3,6,3',4',5',6'-octahydro-2'H-[2,3']-bipyridinyl-1'-carboxylic acid benzyl ester
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: (-)-B-methoxydiisopinocampheylborane / diethyl ether / 1.25 h / -78 - 20 °C
1.2: diethyl ether / -78 - 20 °C / Acid hydrolysis
1.3: 76 percent / aq. NaOH; aq. H2O2 / 3 h / Heating
2.1: 99 percent / Et3N; DMAP / CH2Cl2 / 1.5 h / 20 °C
3.1: 87 percent / NaN3 / dimethylformamide / 2 h / 80 °C
4.1: Ph3P / tetrahydrofuran
4.2: 66 percent / H2O
5.1: 89 percent / Et3N; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C
6.1: 79 percent / Cl2Ru(CHPh)(PCy3)2 / CH2Cl2 / 12 h / Heating
7.1: 98 percent / NaOH / tetrahydrofuran / 2 h / 20 °C
With
(-)-B-methoxydiisopinocamphenylborane; dmap; sodium hydroxide; sodium azide; triethylamine; triphenylphosphine;
Grubbs catalyst first generation;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
1.1: Swern oxidation;
DOI:10.1021/ol0361507