HCID 57751210, compound → HCID 57751169, compound

HRID 658557Notes

Reaction equation

HRID 658557 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, 12 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-97541ded81ba4bc4bfa6621613b37529
Source dataset
uspto-grants-2011_12
Patent number
US08076517B2

Reaction notes

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