Sodium Hydroxide → tert-Butyl 2-Cyclopentylhydrazinecarboxylate

HRID 1098581Notes

Reaction equation

HRID 1098581 reaction equation
C([BH3-])#N.[Na+].[C:5]([O:9][C:10]([NH:12][N:13]=[C:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].[OH-].[Na+]>C(O)(=O)C.CO>[C:5]([O:9][C:10]([NH:12][NH:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4058837N'-cyclopentylidene(tert-butoxy)carbohydrazideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 23113328tert-Butyl 2-CyclopentylhydrazinecarboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (6.4 g, 0.101 mol) was added portion-wise to a suspension of 1-cyclopentylidenehydrazine-2-carboxylic acid tert-butyl ester (20 g, 0.101 mol) in a mixture of acetic acid and methanol (288 mL, 1:1). The resulting solution was stirred at RT for 2 h. The reaction mixture was neutralized with 1 N aq NaOH and extracted with CH2Cl2. The organic layer was washed with saturated NaHCO3, dried (Na2SO4) and concentrated under reduced pressure to give 1-cyclopentylhydrazine-2-carboxylic acid tert-butyl ester (18.4 g) as an oil.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with saturated NaHCO3
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d241d90089c44fb5aaf2fcf740cb8fb0
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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