Benzylamine → ethyl 1,4-dioxo-2-(phenylmethyl)hexahydropyrrolo[1,2-a]pyrazine-8a(6H)-carboxylate

HRID 421207Notes

Reaction equation

HRID 421207 reaction equation
Br[CH2:2][C:3]([N:5]1[CH2:9][CH2:8][CH2:7][C:6]1([C:15]([O:17]CC)=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:4].[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[O:17]=[C:15]1[N:27]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:2][C:3](=[O:4])[N:5]2[CH2:9][CH2:8][CH2:7][C:6]12[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 59215802Diethyl 1-(bromoacetyl)-2,2-pyrrolidinedicarboxylate

Product 1

HCID 59215759ethyl 1,4-dioxo-2-(phenylmethyl)hexahydropyrrolo[1,2-a]pyrazine-8a(6H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of diethyl 1-(bromoacetyl)-2,2-pyrrolidinedicarboxylate (D64, 950 mg) in acetonitrile (10 mL) at r.t, benzylamine (340 microL) was added. The resulting mixture was stirred at r.t. for 3.5 hours: the formation of a white solid was observed. The suspension was then filtered over a Gooch funnel. The organic filtrate was diluted with ethyl acetate (15 mL) and washed with water (2×10 mL). The organic phase was dried and concentrated in vacuo to a residue which was purified by flash chromatography (Cycl/EtOAc from 50/50 to 35:65) to give the desired compound (200 mg) as colourless oil.

Workup

  1. filtrationThe suspension was then filtered over a Gooch funnel
  2. additionThe organic filtrate was diluted with ethyl acetate (15 mL)
  3. washwashed with water (2×10 mL)
  4. customThe organic phase was dried
  5. concentrationconcentrated in vacuo to a residue which
  6. customwas purified by flash chromatography (Cycl/EtOAc from 50/50 to 35:65)

Sources & evidence

ORD record
ord-803ab7ac856941cdbed11fb8e782f600
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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