Sodium Carbonate → [3-(9H-Fluoren-9-ylmethoxycarbonylamino)propyl]methylcarbamic Acid tert-Butyl Ester

HRID 1039823Notes

Reaction equation

HRID 1039823 reaction equation
[C:1]([O:5][C:6](=[O:13])[N:7]([CH2:9][CH2:10][CH2:11][NH2:12])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:21]([O:23][CH2:24][CH:25]1[C:37]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:31]2[C:26]1=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22]>O.O1CCOCC1>[C:1]([O:5][C:6](=[O:13])[N:7]([CH2:9][CH2:10][CH2:11][NH:12][C:21]([O:23][CH2:24][CH:25]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=2[C:32]2[C:37]1=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:22])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 2756543tert-butyl N-(3-aminopropyl)-N-methylcarbamate

Product 1

HCID 66771670[3-(9H-Fluoren-9-ylmethoxycarbonylamino)propyl]methylcarbamic Acid tert-Butyl EsterYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of N-(3-aminopropyl)-N-methylcarbamic acid tert-butyl ester (2.00 g, 10.6 mmol) and sodium carbonate (2.81 g, 26.6 mmol) in water (7 mL) at 0° C. was added a solution of 9-fluorenylmethyl chloroformate (2.75 g, 10.6 mmol) in 1,4-dioxane (5 mL). The resulting mixture was stirred at room temperature for 2 h and then poured into water (10 mL). This mixture was extracted with diethyl ether (2×50 mL) and the combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford a clear oil. The oil was purified by silica gel flash chromatography (0-70% EtOAc in hexanes) to give the title compound (4.24 g, 77% yield) as a clear oil (product contained a minor impurity, but was used without further purification).

Workup

  1. extractionThis mixture was extracted with diethyl ether (2×50 mL)
  2. dry with materialthe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford a clear oil
  6. customThe oil was purified by silica gel flash chromatography (0-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f67cb739f13a414b92f4eae5a6b1a13a
Source dataset
uspto-grants-2013_10
Patent number
US08551978B2

Reaction notes

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