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

반응식

HRID 546485 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c8777d626f9b4526bff323eb4b050885
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935824B2

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