HCID 76528971, compound → (1S,3R,4S)-4-Amino-3-(Boc-amino)-cyclohexane-carboxylic acid ethyl ester

HRID 56426Notes

Reaction equation

HRID 56426 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH:5]1[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N+]=[N-].[H][H]>[Pd].C(OCC)(=O)C>[NH2:1][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH:5]1[NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17]

Participants

5

Reactant 2

HCID 76528971HCID 76528971, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68604200(1S,3R,4S)-4-Amino-3-(Boc-amino)-cyclohexane-carboxylic acid ethyl esterYield 59%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Racemate-ethyl 4-azido-3-(tert-butoxycarbonylamino)cyclohexanecarboxylate (14.0 g, 66 mmol) and 5% palladium on carbon (50% wet, 1.0 g) in ethyl acetate (100 mL) was stirred at room temperature overnight at a hydrogen pressure of ˜1 atm. After the reaction mixture was filtered, the filtrate was concentrated. The resulting oily residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=4:1˜1:1) to thereby give the title compound (2.0 g, 59%) as a yellow solid.

Workup

  1. filtrationAfter the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe resulting oily residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=4:1˜1:1)

Sources & evidence

ORD record
ord-2c33a82840674d95891dbec8de6f91cf
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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