Ethyl 3-azido-4-hydroxycyclohexanecarboxylate → Ethyl 3-amino-4-hydroxycyclohexanecarboxylate

HRID 56427Notes

Reaction equation

HRID 56427 reaction equation
[N:1]([CH:4]1[CH:9]([OH:10])[CH2:8][CH2:7][CH:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:5]1)=[N+]=[N-]>[Pd].C(OCC)(=O)C>[NH2:1][CH:4]1[CH:9]([OH:10])[CH2:8][CH2:7][CH:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:5]1

Participants

4

Reactant 1

HCID 76528982Ethyl 3-azido-4-hydroxycyclohexanecarboxylate

Product 1

HCID 69078398Ethyl 3-amino-4-hydroxycyclohexanecarboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension mixture of Racemate-ethyl 3-azido-4-hydroxycyclohexanecarboxylate (8.0 g, 37.5 mmol) and 5% palladium on carbon (50% wet, 2.0 g) in ethyl acetate (250 mL) was stirred under hydrogen atmosphere (˜1 atm) at room temperature overnight. After the reaction mixture was filtered, the filtrate was concentrated to thereby give the title compound (5.8 g, 83%) as a yellow solid. MS (ES+) C9H17NO3 requires: 187, found: 188 [M+H]+.

Workup

  1. filtrationAfter the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-af4c71875d944f15b7b3ab5d81005cbd
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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