Cyclopentylamine → Methyl 2-(cyclopentylamino)acetate

HRID 79139노트

반응식

HRID 79139 반응식
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH:7]1([NH2:12])[CH2:11][CH2:10][CH2:9][CH2:8]1.C(N(CC)CC)C>C1COCC1>[CH:7]1([NH:12][CH2:2][C:3]([O:5][CH3:6])=[O:4])[CH2:11][CH2:10][CH2:9][CH2:8]1

참가 물질

5

반응물 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 60984Methyl bromoacetate

생성물 1

HCID 22080509Methyl 2-(cyclopentylamino)acetate수율 68.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of methyl bromoacetate (17.4 mL, 188 mmol) in THF (40 mL) was dropwise added to a solution of cyclopentylamine (18.6 mL, 188 mmol) and triethylamine (26.1 mL, 188 mmol) in THF (150 mL) at 0° C. Following addition, the reaction was allowed to reach room temperature and was stirred overnight. The triethylammonium salts were filtered and rinsed with scant THF. The combined filtrates were concentrated in vacuo. The desired product was distilled from the residuals under reduced pressure to yield 20.2 g of compound 225 (68% yield). 1H NMR (500 MHz, CDCl3) δ ppm 3.73 (s, 3 H) 3.41 (s, 2 H) 3.00-3.13 (m, J=12.90, 6.39, 6.39 Hz, 1 H) 1.77-1.87 (m, 2 H), 1.67-1.74 (m, 2 H) 1.48-1.59 (m, 2 H) 1.29-1.41 (m, 2 H) ppm.

후처리

  1. additionaddition
  2. customto reach room temperature
  3. filtrationThe triethylammonium salts were filtered
  4. washrinsed with scant THF
  5. concentrationThe combined filtrates were concentrated in vacuo
  6. distillationThe desired product was distilled from the residuals under reduced pressure

출처 및 근거

ORD 기록
ord-9259a604d1fe41a2ba980c5de40795f8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841312B2

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