Sodium Azide → (1R,3R,4R)-4-Azido-3-hydroxy-cyclohexanecarboxylic acid amide

HRID 1437335Notes

Reaction equation

HRID 1437335 reaction equation
Br[C@H:2]1[CH2:7][CH2:6][C@@H:5]([C:8]([NH2:10])=[O:9])[CH2:4][C@H:3]1[OH:11].[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C=O)C>[N:12]([C@@H:2]1[CH2:7][CH2:6][C@@H:5]([C:8]([NH2:10])=[O:9])[CH2:4][C@H:3]1[OH:11])=[N+:13]=[N-:14]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 58743889(1R,3R,4S)-4-bromo-3-hydroxycyclohexanecarboxylic amide

Product 1

HCID 58743879(1R,3R,4R)-4-Azido-3-hydroxy-cyclohexanecarboxylic acid amideYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1R,3R,4S)-4-Bromo-3-hydroxy-cyclohexanecarboxylic amide (b) (2.31 g, 10.4 mmol) was treated with sodium azide (1.35 g, 20.8 mmol) in DMF (100 mL) at 60° C. for 15.5 hours. The solvent was removed in vacuo and the residue purified by flash column chromatography (Silica gel, DCM:MeOH 0-10%) to give a white solid (1.09 g, 5.93 mmol, 57%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash column chromatography (Silica gel, DCM:MeOH 0-10%)

Sources & evidence

ORD record
ord-aa7b6dcc4131482f847bf872eb31ee17
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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