(1R,2S)-Tranylcypromine → 1,1-Dimethylethyl 4-({[trans-2-phenylcyclopropyl]amino}methyl)hexahydro-1H-azepine-1-carboxylate

HRID 529304

Reaction equation

HRID 529304 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:11]([CH:13]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:14]1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CC(O)=O>[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[NH:10][CH2:11][CH:13]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:15][CH2:14]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 19493(1R,2S)-TranylcypromineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 588702361-Boc-4-formyl-azepane

Product 1

HCID 665716391,1-Dimethylethyl 4-({[trans-2-phenylcyclopropyl]amino}methyl)hexahydro-1H-azepine-1-carboxylateYield 13.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of [trans-2-phenylcyclopropyl]amine (496 mg, 3.72 mmol), 1,1-dimethylethyl 4-formylhexahydro-1H-azepine-1-carboxylate (871 mg, 3.83 mmol) and AcOH (1 μL, 0.017 mmol) in chloroform (5 mL) was stirred at room temperature for 18 hours. Sodium triacetoxyborohydride (950 mg, 4.48 mmol) was added and stirring continued for 18 hours. Upon completion, saturated NaHCO3 was added to the reaction mixture and the mixture was extracted with THF—CHCl3 (2×50 mL). The organics were combined, dried over Na2SO4 and concentrated. The residue was adsorbed onto silica and purified via column chromatography on the ISCO Companion (gradient 0-40% 80:20:2 [CHCl3/MeOH/NH4OH]/CHCl3; 40 g column) to afford the desired product (168 mg, 12%) as a pale yellow oil LC-MS (ES) m/z=345 (M+H)+.

Workup

  1. stirringstirring
  2. waitcontinued for 18 hours
  3. extractionthe mixture was extracted with THF—CHCl3 (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified via column chromatography on the ISCO Companion (gradient 0-40% 80:20:2 [CHCl3/MeOH/NH4OH]/CHCl3; 40 g column)

Sources & evidence

ORD record
ord-120c0c999cd94d99a186cf4a2f5addee
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Linked notes

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