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

HRID 632578ノート

反応式

HRID 632578 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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]+

後処理

  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)

出典と根拠

ORDレコード
ord-a5cf8c47bc324d9b8255c00db019dcb4
出典データセット
uspto-grants-2016_04
特許番号
US09321718B2

反応ノート

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