Potassium Carbonate → [3-(2-Morpholin-4-yl-ethylamino)-benzyl]-carbamic acid isopropyl ester

HRID 1667496

반응식

HRID 1667496 반응식
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](I)[CH:10]=1)([CH3:4])([CH3:3])C.[NH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+].N1CCC[C@H]1C(O)=O>[Cu]I.CS(C)=O>[CH:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:10]=1)([CH3:3])[CH3:4]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 4082852-MorpholinoethylamineHCID 11645663tert-Butyl 3-iodobenzylcarbamate

생성물 1

HCID 67415913[3-(2-Morpholin-4-yl-ethylamino)-benzyl]-carbamic acid isopropyl ester수율 76.3%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
85 °C

실험 절차

A mixture of (3-iodo-benzyl)-carbamic acid tert-butyl ester (272 mg, 0.816 mmol), 4-(2-aminoethyl)morpholine (0.16 mL, 1.225 mmol), K2CO3 (232 mg, 1.679 mmol), CuI (19 mg, 0.10 mmol), L-proline (19 mg, 0.163 mmol) and DMSO (5 mL) was heated at 85° C. for 1 h. The reaction was cooled, poured onto water and the aqueous layer extracted with EtOAc (×3). The organic layers were combined and washed with water, brine and dried (Na2SO4). Chromatography (MeOH/EtOAc) afforded [3-(2-morpholin-4-yl-ethylamino)-benzyl]-carbamic acid isopropyl ester (200 mg) as an orange viscous oil. m/z (M+1) 336.16.

후처리

  1. temperatureThe reaction was cooled
  2. additionpoured onto water
  3. extractionthe aqueous layer extracted with EtOAc (×3)
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)

출처 및 근거

ORD 기록
ord-b1b0976911de4e949281075102bade76
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044041B2

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