Iodine → HCID 59016573, compound

HRID 919013Notes

Reaction equation

HRID 919013 reaction equation
[C:1]([O:5][C:6]([NH:8][N:9]=[C:10]([CH2:15][CH3:16])[C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].II>C(Cl)Cl.[Pd]>[C:1]([O:5][C:6]([NH:8][NH:9][CH:10]([CH2:15][CH3:16])[C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 807IodineHCID 72490845HCID 72490845, compound

Product 1

HCID 59016573HCID 59016573, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

Approximately 10.3 g N′-(1-ethyl-2,2-dimethyl-propylidene)-hydrazinecarboxylic acid tert-butyl ester was mixed with 4.14 g (3.9 mmol) 10% Pd/C in CH2Cl2 under an atmosphere of hydrogen in a Pan shaker for four hours. The reaction was monitored by TLC (I2 indicator), and the crude product was twice chromatographed using 10% ether in hexane to yield N′-(1-ethyl-2,2-dimethyl-propyl)-hydrazinecarboxylic acid tert-butyl ester. 1H NMR (CDCl3, 500 MHz) δ (ppm): 6.05 (br, 1H), 3.9 (br, 1H)), 2.45 (m, 1H), 1.6 (m, 1H), 1.5 (s, 9H), 1.25 (m, 1H), 1.1 (t, 3H), 0.92 (s, 9H).

Workup

  1. customthe crude product was twice chromatographed

Sources & evidence

ORD record
ord-c6ee8aee5d284ed88e723be3a4985c04
Source dataset
uspto-grants-2016_03
Patent number
US09272986B2

Reaction notes

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