Tetrahydrofuran → tert-Butyl cis(+/-)-4-{benzyl[(benzyloxy)carbonyl]amino}-3-[{2-methyl-2-propen-1-yl}oxy]piperidine-1-carboxylate

HRID 1425186ノート

反応式

HRID 1425186 の反応式
[CH2:1]([NH:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C@H:10]1[O:22][CH2:23][C:24]([CH3:26])=[CH2:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Cl[C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34].C1COCC1>O>[CH2:1]([N:8]([C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[C@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:11][C@H:10]1[O:22][CH2:23][C:24]([CH3:26])=[CH2:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 86648620tert-Butyl cis(+/-)-4-(benzylamino)-3-[(2-methyl-2-propen-1-yl)oxy]piperidine-1-carboxylate

生成物 1

HCID 68405960tert-Butyl cis(+/-)-4-{benzyl[(benzyloxy)carbonyl]amino}-3-[{2-methyl-2-propen-1-yl}oxy]piperidine-1-carboxylate収率 90.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

The same operation as in Example (103a) was performed using tert-butyl cis(±)-4-(benzylamino)-3-[(2-methyl-2-propen-1-yl)oxy]piperidine-1-carboxylate obtained in Example (117c) (4.4 g, 12.2 mmol), sodium bicarbonate, benzyl chloroformate (2.81 g, 16 mmol), THF (15 mL) and water (15 mL). The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1) to obtain 5.46 g of the title compound as a colorless oily substance (99%).

後処理

  1. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1)

出典と根拠

ORDレコード
ord-57c6c6bdbeac4d8e8244a4d8c791ab81
出典データセット
uspto-grants-2015_01
特許番号
US08927588B2

反応ノート

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