(2S,6RS)-4-(4-amino-quinazolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester → (3S,5RS)-1-(4-amino-quinazolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one

HRID 1432930Notes

Reaction equation

HRID 1432930 reaction equation
C(OC([N:11]1[CH:16]([CH3:17])[CH2:15][N:14]([CH2:18][C:19]2[CH:28]=[C:27]3[C:22]([C:23]([NH2:29])=[N:24][CH:25]=[N:26]3)=[CH:21][CH:20]=2)[C:13](=[O:30])[C@@H:12]1[CH3:31])=O)C1C=CC=CC=1.[H][H]>[Pd].CO.C(O)(=O)C>[NH2:29][C:23]1[C:22]2[C:27](=[CH:28][C:19]([CH2:18][N:14]3[CH2:15][CH:16]([CH3:17])[NH:11][C@@H:12]([CH3:31])[C:13]3=[O:30])=[CH:20][CH:21]=2)[N:26]=[CH:25][N:24]=1

Participants

6

Reactant 2

HCID 57166330(2S,6RS)-4-(4-amino-quinazolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 57054033(3S,5RS)-1-(4-amino-quinazolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-oneYield 153.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Palladium on carbon (10%, 700 mg) is added to a solution of (2S,6RS)-4-(4-amino-quinazolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (1.62 g, 3.87 mmol) in 20 mL of methanol and 2 mL of acetic acid. The reaction mixture is left to stir in an atmosphere of hydrogen for eight hours. The palladium is filtered off, and the volitale solvents are removed on the rotovap. The crude product (1.7 g, 95%) is isolated as a white solid. The two epimers are separated on silica gel (1% triethylamine/15% methanol/methylene chloride). The minor epimer is assigned as (3S,5R)-1-(4-amino-quinazolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one and the major epimer is assigned as (3S,5S)-1-(4-amino-quinazolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one.

Workup

  1. waitThe reaction mixture is left
  2. filtrationThe palladium is filtered off
  3. customthe volitale solvents are removed on the rotovap

Sources & evidence

ORD record
ord-1e8bf22d43164199bb126c50f2b7e6cc
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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