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

HRID 2280830노트

반응식

HRID 2280830 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-728dfa57ac4249cebc8e34b6f1c275b2
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139534B2

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