HRID369799

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：CC(C)(C)OC(=O)N1CC(=O)O[C@H](c2ccccc2)[C@@H]1c1ccccc1

HCID981230

tert-Butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate

C21H23NO4

HCID2724254

Sodium bis(trimethylsilyl)amide

C6H18NNaSi2

HCID18352491

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)N1[C@@H](Cc2cccc(C3CCC3)c2)C(=O)O[C@H](c2ccccc2)[C@@H]1c1ccccc1

HCID57135938

未命名化合物

收率 54.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

2 次

PROCEDURE

实验过程

According to example 81, 2.50 g of tert-butyl- (2R, 3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (Aldrich) was alkylated with 1.59 g of 3-cyclobutylbenzyl bromide in 80 mL of anhydrous THF using 7.41 mL of 1M sodium bis(trimethylsilyl)amide in THF (Aldrich). The crude product was subjected to flash chromatography on 120 g of silica gel (8:2 hexane:EtOAc) and then recrystallization from EtOH-water to afford 1.90 g (54%) of tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-cyclobutylbenzyl)-4-morpholinecarboxylate as a white powder, m.p. 145-147° C.

WORKUP

后处理

customrecrystallization from EtOH-water

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-a0731c46a2c343749606ce782d6325e2
来源数据集: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06140100
来源说明: uspto-grants-2000_10

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:13][C:12](=[O:14])[O:11][C@H:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@@H:9]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:27]1([C:31]2[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=2)[CH2:34]Br)[CH2:30][CH2:29][CH2:28]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[O:14]=[C:12]1[C@H:13]([CH2:34][C:33]2[CH:36]=[CH:37][CH:38]=[C:31]([CH:27]3[CH2:28][CH2:29][CH2:30]3)[CH:32]=2)[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@@H:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:10]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[O:11]1