tert-Butyl carbazate → HCID 89924517, compound

HRID 1505684Notes

Reaction equation

HRID 1505684 reaction equation
[NH:1]1[C:5]2([CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[CH2:4][CH2:3][C:2]1=[O:12].[C:13]([O:17][C:18]([NH:20][NH2:21])=[O:19])([CH3:16])([CH3:15])[CH3:14].C([BH3-])#N.[Na+]>CC(O)=O.O.[OH-].[Na+]>[C:13]([O:17][C:18]([NH:20][NH:21][CH:8]1[CH2:9][CH2:10][C:5]2([NH:1][C:2](=[O:12])[CH2:3][CH2:4]2)[CH2:6][CH2:7]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 3

HCID 70091tert-Butyl carbazateHCID 5003444Sodium cyanoborohydrideHCID 114125941-Azaspiro(4.5)-decane-2,8-dione

Product 1

HCID 89924517HCID 89924517, compoundYield 150.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1-Aza-spiro[4.5]decane-2,8-dione (Chembridge corporation, 800 mg; 4.78 mmol; 1.0 eq.) and hydrazinecarboxylic acid tert-butyl ester (309 mg; 2.34 mmol; 1.1 eq.) in AcOH (5 mL) was stirred at RT for 5 min. Sodium cyanoborohydride (133 mg; 2.13 mmol; 1.0 eq.) was then added and the reaction mixture was stirred O/N at RT. It was then diluted with water and basified to pH 9 by addition of a 5N solution of NaOH. During the addition, the reaction mixture was maintained at 20° C. by addition of crushed ice. It was extracted with DCM and the combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound as a yellow oil (1.0 g, 98%) which was used without further purification.

Workup

  1. additionDuring the addition
  2. temperaturethe reaction mixture was maintained at 20° C. by addition of crushed ice
  3. extractionIt was extracted with DCM
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-74c7574ca62c4a9e94e272dcfecc8b4f
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

Loading…