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

Reaction equation

HRID 546485 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-c8777d626f9b4526bff323eb4b050885
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Linked notes

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