Triethylamine → (R)-1-(2-Amino-5-bromo-pyridin-3-ylmethyl)pyrrolidine-2-carboxylic acid methyl ester

HRID 1362060노트

반응식

HRID 1362060 반응식
Br.[Br:2][C:3]1[CH:4]=[C:5]([CH2:10]Br)[C:6]([NH2:9])=[N:7][CH:8]=1.Cl.[CH3:13][O:14][C:15](=[O:21])[C@H:16]1[CH2:20][CH2:19][CH2:18][NH:17]1.C(N(CC)CC)C>CC#N.O>[CH3:13][O:14][C:15]([C@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[CH2:10][C:5]1[C:6]([NH2:9])=[N:7][CH:8]=[C:3]([Br:2])[CH:4]=1)=[O:21]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 44629857Methyl D-prolinate hydrochlorideHCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

생성물 1

HCID 59456924(R)-1-(2-Amino-5-bromo-pyridin-3-ylmethyl)pyrrolidine-2-carboxylic acid methyl ester수율 90.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매2회

실험 절차

A suspension of 5-bromo-3-bromomethyl-pyridin-2-ylamine hydrobromide (8.00 g, 23.1 mmol) and D-proline methyl ester hydrochloride (4.53 g, 27.4 mmol) in CH3CN (100 mL) was treated with a solution of triethylamine (10.4 mL, 74.0 mmol) in CH3CN (100 mL). After stirring at room temperature for 5 h, the cloudy mixture was diluted with H2O (300 mL) and extracted with EtOAc (3×200 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 99:1 to 98:2) gave the title compound (6.55 g, 90%) as a colorless oil: MS (ESI) m/e 314 (M+H)+

후처리

  1. extractionextracted with EtOAc (3×200 mL)
  2. washThe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customPurification by flash column chromatography (silica gel, CH2Cl2/MeOH, 99:1 to 98:2)

출처 및 근거

ORD 기록
ord-7a63368de50e4768acee0fd77132dafe
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879872B2

반응 노트

불러오는 중…