Water → Tert-butyl 3-(benzylamino)-3-(2-fluorobenzyl)cyclohexylcarbamate

HRID 530893Notes

Reaction equation

HRID 530893 reaction equation
[CH2:1]([N:8]=[C:9]1[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[CH2:26][Mg]Cl.CCOCC.O>C1COCC1>[CH2:1]([NH:8][C:9]1([CH2:26][C:25]2[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=2[F:23])[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 67983484Tert-butyl 3-(benzylimino)cyclohexylcarbamateHCID 178505627HCID 178505627, compound

Product 1

HCID 67983661Tert-butyl 3-(benzylamino)-3-(2-fluorobenzyl)cyclohexylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of tert-butyl 3-(benzylimino)cyclohexylcarbamate (4 mmol) in THF (10 mL) was added a solution of (2-fluorobenzyl)magnesium chloride in ether (9 mmol, 0.25 M, 36 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for overnight. The reaction mixture was added to the iced water. The organics were extracted using EtOAc from the aqueous mixture. The EtOAc solution was concentrated. The product, tert-butyl 3-(benzylamino)-3-(2-fluorobenzyl)cyclohexylcarbamate, was purified by column chromatography on silica gel.

Workup

  1. extractionThe organics were extracted
  2. concentrationThe EtOAc solution was concentrated
  3. customThe product, tert-butyl 3-(benzylamino)-3-(2-fluorobenzyl)cyclohexylcarbamate, was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ee52f911baa84fcf90879aae4e6c04ec
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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