HCID 57751210, compound → HCID 57751169, compound

HRID 335666Notes

Reaction equation

HRID 335666 reaction equation
[C:1]([O:5][C:6]([NH:8][NH:9][C@H:10]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:11][CH:12]=[CH2:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.O.[Pd]>[C:1]([O:5][C:6]([NH:8][NH:9][C@H:10]([C:14]([CH3:15])([CH3:17])[CH3:16])[CH2:11][CH2:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 57751210HCID 57751210, compound

Product 1

HCID 57751169HCID 57751169, compoundYield 92.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(S)—N′-(1-tert-Butyl-but-3-enyl)-hydrazinecarboxylic acid tert-butyl ester (2.34 g, 9.65 mmoles) was dissolved in methanol (50 mL) in a Parr bottle. 10% Pd/C (70 mg) was added as a slurry in water (1.6 mL), and the mixture was shaken on a Parr hydrogenator for 4.5 h with a starting pressure of 55 psi. The pressure dEcREase was monitored as a measure of the reaction progress, indicating that the reaction was likely complete after 30 minutes. The catalyst was allowed to substantially settle, and the supernatant was removed with a pipette, passed through a 0.45 micron syringe filter, and analyzed by TLC. Solvent was removed in vacuo to yield 2.19 g (92.7%) of (S)—N′-(1-tert-butyl-butyl)-hydrazinecarboxylic acid tert-butyl ester as a faintly pale yellow oil. Rf=0.48 (5:1 hexanes:ethyl acetate, I2 visualization), 1H NMR (400 MHz, CDCl3).6.0 (br, 1H), 4.0 (br, 1H), 2.5 (d, 1H), 1.5 (s, 9H), 1.1 (m, 2H), 1.6 (br, 2H), 0.94 (s, 9H), 0.94 (t, 3H).

Workup

  1. waitwas likely complete after 30 minutes
  2. customthe supernatant was removed with a pipette
  3. filtrationfilter
  4. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-263cab1224ca4811ba517004e4724eff
Source dataset
uspto-grants-2014_11
Patent number
US08884060B2

Reaction notes

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