HRID1963641

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID21225753

未命名化合物

结构：COC(=O)N1CC[C@H](c2cc(=O)[nH]o2)C[C@@H]1Cc1ccc(C(F)(F)F)c(F)c1

HCID66734831

未命名化合物

PRODUCTS

生成物

HCID66732432

未命名化合物

收率 45%

HCID66734831

未命名化合物

收率 46%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

2 次

PROCEDURE

实验过程

Cis-methyl 2-(3-fluoro-4-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)-piperidine-1-carboxylate (1.32 g, 3.28 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak AD (250×20), 5 μm particle size, mobile phase: Heptane/EtOH 85/15, flow rate 18 mL/min) to yield (2R,4S)-methyl 2-(3-fluoro-4-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (594 mg, 46%), Chiral purity 99.5% ee, Optical rotation [α]D20=+9.1 (acetonitrile, c=1) and (2S,4R)-methyl 2-(3-fluoro-4-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (589 mg, 45%), Chiral purity 99.2% ee, Optical rotation [α]D20=−8.8 (acetonitrile, c=1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-1e27fa4ef6314e889875d28fefa90033
来源数据集: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08415378B2
来源说明: uspto-grants-2013_04

反应 SMILES

[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[C:25]([F:28])([F:27])[F:26])[CH2:5][C@H:6]1[CH2:11][C@@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][N:7]1[C:18]([O:20][CH3:21])=[O:19].CCCCCCC.CC(O)C>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[C:25]([F:27])([F:26])[F:28])[CH2:5][C@H:6]1[CH2:11][C@@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][N:7]1[C:18]([O:20][CH3:21])=[O:19].[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[C:25]([F:27])([F:26])[F:28])[CH2:5][C@@H:6]1[CH2:11][C@H:10]([C:12]2[O:16][NH:15][C:14](=[O:17])[CH:13]=2)[CH2:9][CH2:8][N:7]1[C:18]([O:20][CH3:21])=[O:19]