Methylamine → 7-Methylamino-3,4,4a,9a-tetrahydro-1H-benzo[4,5]furo[2,3-c]pyridine-2-carboxylic acid tert-butyl ester

HRID 1616900Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]2[CH:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]3[O:21][C:4]=2[CH:3]=1.CC1C=CC2C=CC3C=C[C:32](C)=[N:33]C=3C=2N=1.CN>CN(C=O)C.C1COCC1.[Cu]I>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][CH:8]2[C:5]3[CH:6]=[CH:7][C:2]([NH:33][CH3:32])=[CH:3][C:4]=3[O:21][CH:9]2[CH2:10]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 80 °C

Procedure

Anhydrous DMF was sparged with argon gas for 1 h before being used. Tert-butyl 7-iodo-3,4,4a,9a-tetrahydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate (1 g, 2.5 mmol) sodium tert-butoxide (723 mg, 7.5 mmol), neocuproine (52 mg, 0.25 mmol) and copper (I) iodide (290 mg, 1.5 mmol) were dissolved in anhydrous DMF (20 mL). To this mixture was added a 2M solution of methylamine in THF (6 mL) and the reaction shaken at 80° C. for 16 h. The solvent was evaporated and the residue dissolved in DCM and washed with H2O (3×). The solvent was evaporated and the crude residue used as such in the next reaction step.

Workup

customAnhydrous DMF was sparged with argon gas for 1 h
customThe solvent was evaporated
dissolutionthe residue dissolved in DCM
washwashed with H2O (3×)
customThe solvent was evaporated
customsuch in the next reaction step

Sources & evidence

ORD record: ord-5a0c53f20a0f4682aee98e909b6965c0
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765779B2

Reaction notes

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