Ammonium Chloride → Tert-butyl 3-(2-fluorobenzyl)-3-hydroxycyclohexylcarbamate

HRID 530839노트

반응식

HRID 530839 반응식
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1.[F:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[CH2:19][Mg]Br.[NH4+].[Cl-]>C(OCC)C>[F:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[CH2:19][C:2]1([OH:1])[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:3]1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 44228975(3-Oxo-cyclohexyl)-carbamic acid tert-butyl esterHCID 178505626HCID 178505626, 화합물

생성물 1

HCID 67983409Tert-butyl 3-(2-fluorobenzyl)-3-hydroxycyclohexylcarbamate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of tert-butyl 3-oxocyclohexylcarbamate (2 mmol, 426 mg) in ethyl ether (10 mL) was added a solution of (2-fluorobenzyl)magnesium bromide in ether (5 mmol, 0.25 M, 20 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for overnight. The reaction mixture was added to the NH4Cl aqueous solution. The organics were extracted with EtOAc. The EtOAc solution was concentrated. The product, tert-butyl 3-(2-fluorobenzyl)-3-hydroxycyclohexylcarbamate was purified by column chromatography on silica gel.

후처리

  1. extractionThe organics were extracted with EtOAc
  2. concentrationThe EtOAc solution was concentrated
  3. customThe product, tert-butyl 3-(2-fluorobenzyl)-3-hydroxycyclohexylcarbamate was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-14bd62da0f6a4a509fc40a1b6d0c9bb2
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09351965B2

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