Dicyclohexylcarbodiimide → tert-Butyl 4-[(2R)-2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl]piperazine-1-carboxylate

HRID 2375259Notes

Reaction equation

HRID 2375259 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[C:11]([OH:13])=O.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[N:39]1([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1>C(#N)C>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[C:11]([N:42]1[CH2:41][CH2:40][N:39]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:44][CH2:43]1)=[O:13]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 687062(R)-1,4-Benzodioxane-2-carboxylic acid

Product 1

HCID 29974548tert-Butyl 4-[(2R)-2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl]piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5 g of (2R)-2,3-dihydro-1,4-benzodioxin-2-carboxylic acid (27.8 mmol) are dissolved in 300 ml of acetonitrile. 6 g of N,N′-dicyclohexylcarbodiimide (29.1 mmol) and then 4.1 g of 1-hydroxybenzotriazole (30.6 mmol) are added. Finally, 6.2 g of tert-butyl piperazine-1-carboxylate (33.4 mmol) are added and stirring is carried out for 12 hours at ambient temperature. The reaction mixture is subsequently filtered and the filtrate is then evaporated to dryness. The oil thereby obtained is purified by flash chromatography on silica (eluant: toluene/ethyl acetate 80/20) to yield the expected product in the form of an oil.

Workup

  1. filtrationThe reaction mixture is subsequently filtered
  2. customthe filtrate is then evaporated to dryness
  3. customThe oil thereby obtained
  4. customis purified by flash chromatography on silica (eluant: toluene/ethyl acetate 80/20)

Sources & evidence

ORD record
ord-c884679efa394058a825853346468609
Source dataset
uspto-grants-2008_12
Patent number
US07465733B2

Reaction notes

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