Sodium hydride → HCID 86585293, compound

HRID 1249810Notes

Reaction equation

HRID 1249810 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)=O)C1C=CC=CC=1.[H-].[Na+].[H][H].Br[CH2:23][C:24]([C:26]12[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2)=[O:25]>O.CN(C)C=O>[O:25]=[C:24]([C:26]12[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2)[CH2:23][N:14]1[CH2:15][CH2:16][NH:11][CH2:12][C:13]1=[O:17]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 197820Bromomethyl tricyclo[3.3.1.13,7]dec-1-yl ketoneHCID 736777Benzyl 3-oxopiperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86585293HCID 86585293, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a round bottomed flask were added 4-benzyloxycarbonylpiperazin-2-one (234.26 mg, 1.0 mmol) along with N,N-dimethylforamide(5.0 ml), and sodium hydride (73.0 mg (60%), 1.0 mmol). After the evolution of hydrogen had ceased the reaction was allowed to stir for an additional 30 minutes. To this was added 1 adamantyl bromomethyl ketone(257.18 mg, 1.0 mmol). The reaction stirred at Rt. for 18 hrs. The reaction was poured into water(25ml) and extracted with ethylacetate(2×25 ml). The ethylacetate layer was washed with brine and dried (MgSO4). Solvent removal yielded 4-benzyloxycarbonyl-[1-(2-oxo-2-(adamant-1-yl)ethyl]piperazin-2-one. 400 Mhz H1 NMR (CDCl3): 1.68-1.91(m,12H), 2.06 (br s,3H), 3.32(t,2H), 3.77(t,2H), 4.20(s,2H), 4.34(s,2H), 5.16(s,2H), 7.36(m,5H). The material was used with out further purification.

Workup

  1. stirringThe reaction stirred at Rt
  2. waitfor 18 hrs
  3. extractionextracted with ethylacetate(2×25 ml)
  4. washThe ethylacetate layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customSolvent removal

Sources & evidence

ORD record
ord-e0ba3bf1e07945f5960af79932de84c4
Source dataset
uspto-grants-2002_01
Patent number
US06335343B1

Reaction notes

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