(+)-Tranylcypromine → HCID 11480594, compound

HRID 1260455Notes

Reaction equation

HRID 1260455 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.O[C@@H]([C@H](O)C(O)=O)C(O)=O.[C:23]1([C@H:29]2[CH2:31][C@@H:30]2[NH2:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:32]([C@H:30]1[CH2:31][C@@H:29]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[C:5]=[O:11]

Participants

6

Reactant 4

HCID 26070(+)-TranylcypromineHCID 94429TriphosgeneHCID 439655D-Tartaric acidHCID 516892Sodium Bicarbonate

Product 1

HCID 11480594HCID 11480594, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triphosgene (0.33 eq.) was added to a stirred, cooled 0° C., 0.053 M mixture of (2S,3S)-2,3-dihydroxysuccinic acid and (1S,2R)-2-phenylcyclopropanamine (1:1) (prepared according to: Newman in “Optical resolution procedures for chemical compounds” Chapter 1 Amines and related com. Pages 120-122) in a 1:1 mixture of DCM and sat. aq. NaHCO3 solution, and the reaction mixture was stirred at 0° C. for 1 h. The reaction was poured into a separatory funnel and layers were separated. Aqueous layer was extracted with DCM (×3). Combined organic layers were dried and evaporated to give the title compound as colorless oil in quantitative yield. 1H NMR (300 MHz, CDCl3, 300K) δ 7.30 (2H, t, J=7.0 Hz), 7.21 (1H, t, J=7.0 Hz), 7.05 (2H, d, J=7.0 Hz), 2.92 (1H, ddd, J=7.4, 4.3, 3.3 Hz), 2.20 (1H, ddd, J=9.8, 6.8, 3.3 Hz), 1.33-1.20 (2H, m).

Workup

  1. additionThe reaction was poured into a separatory funnel
  2. customlayers were separated
  3. extractionAqueous layer was extracted with DCM (×3)
  4. customCombined organic layers were dried
  5. customevaporated

Sources & evidence

ORD record
ord-2a092cbe7b144ed5b6367cb589b1b9ab
Source dataset
uspto-grants-2013_06
Patent number
US08470823B2

Reaction notes

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