Potassium Carbonate → HCID 67510086, compound

HRID 1400054Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH:13]([CH2:14][O:15][CH3:16])[CH:12]2[CH2:11][N:10]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:9]3)=[CH:4][CH:3]=1.[NH:24]1[CH2:28][CH2:27][CH2:26][C:25]1=[O:29].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Cu]I>[CH3:16][O:15][CH2:14][CH:13]1[C:8]2([C:5]3[CH:6]=[CH:7][C:2]([N:24]4[CH2:28][CH2:27][CH2:26][C:25]4=[O:29])=[CH:3][CH:4]=3)[CH:12]1[CH2:11][N:10]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:9]2

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of tert-butyl 1-(4-bromophenyl)-6-(methoxymethyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylate (Intermediate IX, 890 mg, 2.33 mmol) in 1,4-dioxane (15 mL), was added 2-pyrrolidinone (0.177 mL, 2.33 mmol), (±)-trans-1,2-diamine (0.139 mL, 1.16 mmol), CuI (221.3 mg, 1.16 mmol) and potassium carbonate (643 mg, 4.66 mmol) under nitrogen atmosphere. The reaction mixture was heated at 120° C. for 36 h. After completion of the reaction as confirmed by TLC, the solvent was removed in vacuo to afford the crude compound, which was purified by column chromatography (silica gel, 2:8 EtOAc:Pet. ether) to afford pure tert-butyl 6-(methoxymethyl)-1-(4-(2-oxopyrrolidin-1-yl)phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylate (600 mg, 66%) as a viscous oil.

Workup

customAfter completion of the reaction
customthe solvent was removed in vacuo
customto afford the crude compound, which
customwas purified by column chromatography (silica gel, 2:8 EtOAc:Pet. ether)

Sources & evidence

ORD record: ord-d97b33e3325543edaf62ce8264237d60
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906913B2

Reaction notes

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