Ethyl 1-aminocyclopropane-1-carboxylate hydrochloride → (1R*,2S*)-N,N-Bis(tert-butoxycarbonyl)-4-[(1-ethoxycarbonyl)cyclopropan-1-yl]amino-1,2-cyclohexanediamine

HRID 546485

反応式

HRID 546485 の反応式
Cl.[NH2:2][C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1.[C:11]([O:15][C:16]([N:18]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@@H:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][C@@H:20]1[NH2:26])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[C:30]([O:29][C:27]([N:18]([C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])[C@@H:19]1[CH2:24][CH2:23][CH:22]([NH:2][C:3]2([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]2)[CH2:21][C@@H:20]1[NH2:26])=[O:28])([CH3:33])([CH3:32])[CH3:31]

参加物

6

反応物 4

HCID 386203Ethyl 1-aminocyclopropane-1-carboxylate hydrochlorideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68905437(1R*,2S*)-N,N-bis(tert-butoxycarbonyl)-4-oxo-1,2-cyclohexanediamine

生成物 1

HCID 68910855(1R*,2S*)-N,N-Bis(tert-butoxycarbonyl)-4-[(1-ethoxycarbonyl)cyclopropan-1-yl]amino-1,2-cyclohexanediamine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Ethyl 1-aminocyclopropanecarboxylate hydrochloride (1.63 g) was dissolved in dichloromethane (60 ml), and (1R*,2S*)-N,N-bis(tert-butoxycarbonyl)-4-oxo-1,2-cyclohexanediamine (3.0 g) and sodium triacetoxy-borohydride (2.51 g) were added to stir the mixture at room temperature for 3 hours. An aqueous solution of sodium hydrogencarbonate was added to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1→1:1) to obtain the title compounds (Stereoisomer A: 1.43 g and Stereoisomer B: 2.17 g) as colorless amorphous solids.

後処理

  1. customto separate an organic layer
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1→1:1)

出典と根拠

ORDレコード
ord-c8777d626f9b4526bff323eb4b050885
出典データセット
uspto-grants-2011_05
特許番号
US07935824B2

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