HRID657138

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID3776

Isopropanol

C3H8O

结构：CC(C)(C)OC(=O)N1CCC(O)C(CNC(=O)OCc2ccccc2)C1

HCID68810490

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N1CC[C@H](O)[C@H](CNC(=O)OCc2ccccc2)C1

HCID86635364

未命名化合物

HCID86635365

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID280

Carbon dioxide

CO2

PROCEDURE

实验过程

1,1-Dimethylethyl 4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate was resolved via supercritical fluid chromatography (SFC) using a Chiralpak AD-H 30×250 mm column (20% Isopropanol in CO2; 70 ml/min; 30 deg C.; uv 220 nm) to obtain the E1 (first eluting isomer: 98% ee) and E2 (second eluting isomer; 94% ee) enantiomers presumed 1,1-dimethylethyl (3S,4R)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate (E2) and presumed 1,1-dimethylethyl (3R,4S)-4-hydroxy-3-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-piperidinecarboxylate (E1) as white solids.

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-41af00076c374fb481be0e84c590c566
来源数据集: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08071592B2
来源说明: uspto-grants-2011_12

反应 SMILES

[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C(O)(C)C>C(=O)=O>[OH:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18].[OH:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@@H:3]1[CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18]