Benzyl Alcohol → Benzyl (4-methoxybicyclo[2.2.2]octan-1-yl)carbamate

HRID 2280830ノート

反応式

HRID 2280830 の反応式
[CH3:1][O:2][C:3]12[CH2:10][CH2:9][C:6](C(O)=O)([CH2:7][CH2:8]1)[CH2:5][CH2:4]2.CC[N:16]([CH:20](C)C)C(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.[C:40]1([CH2:46][OH:47])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O1CCOCC1>[CH2:46]([O:47][C:20](=[O:30])[NH:16][C:6]12[CH2:5][CH2:4][C:3]([O:2][CH3:1])([CH2:8][CH2:7]1)[CH2:10][CH2:9]2)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 127651534-Methoxybicyclo(2.2.2)octane-1-carboxylic acid

生成物 1

HCID 86676359Benzyl (4-methoxybicyclo[2.2.2]octan-1-yl)carbamate収率 96%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-methoxybicyclo[2.2.2]octane-1-carboxylic acid (5.9 g, 32 mmol) in dioxane (80 mL) was added DIEA (8.3 g, 64.2 mmol), diphenyl phosphoryl azide (13.2 g, 48 mmol) and phenylmethanol (17.3 g, 160 mmol). The mixture was stirred at 80° C. overnight and then concentrated under reduce pressure. The residue was purified by silica gel column chromatography (5% methanol in DCM) to give the desired product. (9 g, 31 mmol, yield 96%). MS (ESI) m/z=290.2 [M+H]+.

後処理

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel column chromatography (5% methanol in DCM)

出典と根拠

ORDレコード
ord-728dfa57ac4249cebc8e34b6f1c275b2
出典データセット
uspto-grants-2015_09
特許番号
US09139534B2

反応ノート

読み込み中…