Ethyl Acetate → 1-Cyclopentyl 1-{[3-(bromomethyl)benzyl]amino}cyclopentanecarboxylate

HRID 632578노트

반응식

HRID 632578 반응식
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[CH:11]1([O:16][C:17](=[O:24])[C:18]2([CH2:23][CH2:22][CH2:21][CH2:20]2)[NH2:19])[CH2:15][CH2:14][CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OCC)(=O)C>ClC(Cl)C>[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH:19][C:18]1([C:17]([O:16][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:24])[CH2:20][CH2:21][CH2:22][CH2:23]1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 71278253-(Bromomethyl)benzaldehydeHCID 581390221-Cyclopentyl 1-aminocyclopentanecarboxylate

생성물 1

HCID 866864281-Cyclopentyl 1-{[3-(bromomethyl)benzyl]amino}cyclopentanecarboxylate수율 61.2%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of 3-(bromomethyl)-benzaldehyde (0.467 g, 2.44 mmol) in dichloroethane (20 mL) was added cycloleucine cyclopentyl ester (0.802 g, 4.06 mmol) and sodium triacetoxyborohydride (1.18 g, 5.56 mmol). The mixture was stirred at room temperature for 3 hours, then poured into ethyl acetate (200 mL) and washed with saturated ammonium chloride solution (3 times 50 mL). The organic fraction was dried (MgSO4), concentrated and purified by flash column chromatography (SiO2, 7:3 heptane:ethyl acetate) to yield the desired product (0.568 g, 61% yield). LC/MS: m/z 380/382 [M+H]+

후처리

  1. washwashed with saturated ammonium chloride solution (3 times 50 mL)
  2. dry with materialThe organic fraction was dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by flash column chromatography (SiO2, 7:3 heptane:ethyl acetate)

출처 및 근거

ORD 기록
ord-a5cf8c47bc324d9b8255c00db019dcb4
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321718B2

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