Lithium Hydroxide → HCID 58822143, compound

HRID 546477Notes

Reaction equation

HRID 546477 reaction equation
[N:1]([C@@H:4]1[C@@H:9]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][CH2:7][C@@H:6]([C:18]([O:20]CC2C=CC=CC=2)=[O:19])[CH2:5]1)=[N+:2]=[N-:3].[OH-].[Li+]>O1CCCC1.O>[N:1]([C@@H:4]1[C@@H:9]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[CH2:8][CH2:7][C@@H:6]([C:18]([OH:20])=[O:19])[CH2:5]1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86593064HCID 86593064, compound

Product 1

HCID 58822143HCID 58822143, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzyl (1R,3S,4S)-3-azido-4-(N-tert-butoxycarbonylamino)cyclohexane-1-carboxylate (4.4 g) was dissolved in tetrahydrofuran (160 ml) and water (20 ml), and lithium hydroxide (366 mg) was added under ice cooling. After 10 minutes, the mixture was heated to room temperature to continue stirring. After 20 hours, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:10) to obtain the title compound (1.86 g) as a pale yellow oil.

Workup

  1. waitAfter 20 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:10)

Sources & evidence

ORD record
ord-24b3b04f4b8147d5913b8e724c663cda
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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