Di-tert-butyl dicarbonate → HCID 68671142, compound

HRID 2071034Notes

Reaction equation

HRID 2071034 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[C:9]([C:11]([CH3:13])=[CH2:12])[CH:8]=[C:7]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=1)=[N+]=[N-].[O:22](C(OC(C)(C)C)=O)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=O>CCOC(C)=O.[Pd]>[CH2:15]([O:14][C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:8]=1)[CH2:4][NH:1][C:23](=[O:22])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 91315367HCID 91315367, compound

Product 1

HCID 68671142HCID 68671142, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 573 mg (1.97 mmol) of 1-(azidomethyl)-3-(benzyloxy)-5-(prop-1-en-2-yl)benzene, 0.5 mL of BOC2O, and 60.5 mg of 10% Pd/C in 10 mL of EtOAc was stirred at r.t. under H2 balloon for 11.5 h. The mixture was filtered through Celite and concentrated. Purification by flash silica gel chromatography (10% EtOAc/hexanes) provided 336 mg of tert-butyl 3-(benzyloxy)-5-isopropylbenzylcarbamate in 62% yield.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customPurification by flash silica gel chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7e447c9ea0d740de8a619a2d6668baaa
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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