Sodium Bicarbonate → [1-(4-Bromophenyl)-cyclopropyl]-propylamine

HRID 51771Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH:11][C:12](=O)[CH2:13][CH3:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([NH:11][CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of N-[1-(4-bromophenyl)-cyclopropyl]-propionamide (Intermediate 117, 85.0 mg, 0.32 mmol) in THF (5 mL) at 0° C. was added BH3—Me2S (48.0 mg, 0.63 mmol; 0.31 mL of a 2M solution in THF). The solution was heated to 55° C. for 17 hours, cooled to room temperature, saturated aqueous NaHCO3 was added and the resulting mixture was stirred for 2 hours. This mixture was extracted with EtOAc and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound was isolated by column chromatography (10-30% EtOAc-hexanes).

Workup

temperaturecooled to room temperature
extractionThis mixture was extracted with EtOAc
washthe combined organic layers were washed with H2O and saturated aqueous NaCl
dry with materialbefore being dried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-b6b6b1bcfcc34db3a3f779b3d83412d0
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713647B2

Reaction notes

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