Di-tert-butyl dicarbonate → Di-tert-butyl dicarbonate

HRID 611216Notes

Reaction equation

HRID 611216 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:2]1.[C:22]([O:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>ClCCl>[C:25]([O:24][C:22]([N:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:8][CH2:7][CH2:6][C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)=[O:23])([CH3:28])([CH3:27])[CH3:26].[C:30]([O:29][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([O:32][C:33]([CH3:35])([CH3:36])[CH3:34])=[O:31]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 19600136HCID 19600136, compound

Product 2

HCID 90495Di-tert-butyl dicarbonateHCID 19600203HCID 19600203, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the above crude N-[3-(3-furyl)propyl]-6-phenylhexylamine in 100 ml of dichloromethane, 2.49 g (11.4 mmol) of di-tert-butyl dicarbonate was added, followed by stirring at room temperature for 2 hours. The solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to yield N-(tert-butoxycarbonyl)-N-[3-(3-furyl)propyl]-6-phenylhexylamine as a mixture with di-tert-butyl dicarbonate.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-24363952d8c041c796611c0893883795
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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