2-(2-(((1,1-Dimethylethyl)dimethylsilyl)oxy)ethyl)-3-(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)-1-azidocyclobutane → 2-(2-(((1,1-Dimethylethyl)dimethylsilyl)oxy)ethyl)-3-(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)-1-aminocyclobutane

HRID 465764Notes

Reaction equation

HRID 465764 reaction equation
[CH3:1][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][CH2:7][CH2:8][CH:9]1[CH:12]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][CH:10]1[N:22]=[N+]=[N-])([CH3:4])[CH3:3]>CO.[Pd]>[CH3:4][C:2]([Si:5]([CH3:25])([CH3:26])[O:6][CH2:7][CH2:8][CH:9]1[CH:12]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][CH:10]1[NH2:22])([CH3:1])[CH3:3]

Participants

4

Reactant 1

HCID 197942502-(2-(((1,1-Dimethylethyl)dimethylsilyl)oxy)ethyl)-3-(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)-1-azidocyclobutane

Product 1

HCID 197942612-(2-(((1,1-Dimethylethyl)dimethylsilyl)oxy)ethyl)-3-(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)-1-aminocyclobutane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-(2-(((1,1-Dimethylethyl)dimethylsilyl)oxy)ethyl)-3-(((1,1-dimethylethyl)dimethyl-silyl)oxymethyl)-1-azidocyclobutane (980 mg, 2.45 mmol), prepared as described in Step D above, was dissolved in 20 mL of methanol and an excess of palladium on carbon was added to the solution under a nitrogen atmosphere. The reaction mixture was stirred at ambient temperature and atmospheric pressure under hydrogen for 0.5 h. The catalyst was removed by filtration and washed with 10 mL of methanol. The filtrate was concentrated in vacuo to give 850 mg (93%) yield of the title compound; MS DCI-NH3M/Z: 374 (M+H)+, 391 (M+NH4)+.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with 10 mL of methanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bbd4a6b6502a420e8170dc9eab4d60d3
Source dataset
uspto-grants-1992_10
Patent number
US05153352

Reaction notes

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