Water → (9H-Fluoren-9-yl)methyl 3-oxopiperazine-1-carboxylate

HRID 1619330Notes

Reaction equation

HRID 1619330 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].C([O-])([O-])=O.[Na+].[Na+].O.[C:15](Cl)([O:17][CH2:18][CH:19]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16]>O1CCOCC1.[Na+].[Cl-]>[O:7]=[C:2]1[NH:1][CH2:6][CH2:5][N:4]([C:15]([O:17][CH2:18][CH:19]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[C:26]3[C:31]2=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:16])[CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 231360Piperazin-2-one

Product 1

HCID 49760364(9H-Fluoren-9-yl)methyl 3-oxopiperazine-1-carboxylateYield 103.9%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of piperazin-2-one (2 g, 20 mmol, 1 equiv), Na2CO3 (4.2 g, 40 mmol, 2 equiv) and water (20 mL) in 1,4-dioxane (60 mL) was added Fmoc-Cl (5.7 g, 22 mmol, 1.1 equiv) at 0° C. After the reaction mixture was stirred at room temperature for 4 h, it was diluted with saturated NaCl (200 mL). The solution was extracted with ethyl acetate (3×50 mL) and dried over Na2SO4. The combined organic layers were concentrated to give 6.7 g of the desired product, which was directly used for the next step without further purification. MS (ESI): 323 (MH+).

Workup

  1. extractionThe solution was extracted with ethyl acetate (3×50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-ee728980c8ca4fcdba6d775252948adc
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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