HCID 69025420, compound → HCID 69024885, compound

HRID 1433054Notes

Reaction equation

HRID 1433054 reaction equation
C(OC(=O)[CH2:5][NH:6][CH2:7][C@H:8]([NH:12][C:13]([O:15]CC1C=CC=CC=1)=O)[CH:9]([CH3:11])[CH3:10])C.[H][H]>CO.[Pd]>[CH:9]([C@H:8]1[NH:12][C:13](=[O:15])[CH2:5][NH:6][CH2:7]1)([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 69025420HCID 69025420, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69024885HCID 69024885, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a Parr vessel charged with (R)-(2-benzyloxycarbonylamino-3-methyl-butylamino)-acetic acid ethyl ester (4.2 g, 13.0 mmol) in MeOH (130 mL) is added Pd-on-C (10%, 396 mmol). The reaction vessel is pressurized with 40 PSI hydrogen pressure and shaken for 4 h at ambient temperature. The reaction mixture is then filtered through celite and the filtrate is concentrated to provide 1.77 g (95%) of (R)-6-isopropyl-piperazin-2-one as an off-white solid which is used without further purification. 1H NMR (300 MHz, CDCl3) δ0.93 (d, J=6.8 Hz, 3H), 0.97 (d, J=6.8 Hz, 3H), 1.68 (sept, J=6.7 Hz, 1H), 2.67 (dd, J=12.8, 8.9 Hz, 1H), 3.09-3.22 (m, 2H), 3.46 (ABq, ΔAB=34.3 Hz, JAB=17.5 Hz, 2H), 5.97 (br s, 1H) ppm.

Workup

  1. filtrationThe reaction mixture is then filtered through celite
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-e298df93cc64470bb7ec2bc3535b107a
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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