1,2-Dichloroethane → HCID 89709467, compound

HRID 717902Notes

Reaction equation

HRID 717902 reaction equation
[CH:1]1([CH:7]2[CH:16]3[CH2:17][CH2:18][CH2:19][O:20][CH:15]3[C:14]3[CH:13]=[C:12]([C:21]([OH:23])=[O:22])[CH:11]=[CH:10][C:9]=3[NH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(N)CC1.CCN(C(C)C)C(C)C.C(Cl)CCl>C(Cl)Cl>[CH:1]1([C@H:7]2[C@@H:16]3[CH2:17][CH2:18][CH2:19][O:20][C@@H:15]3[C:14]3[CH:13]=[C:12]([C:21]([OH:23])=[O:22])[CH:11]=[CH:10][C:9]=3[NH:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 89709503HCID 89709503, compound

Product 1

HCID 89709467HCID 89709467, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4aSR*,5SR*,10bSR*)-5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline-9-carboxylic acid (50 mg, 0.16 mmol, 1 equiv.) in dry CH2Cl2 (1.6 mL) under argon atmosphere at 0° C. was added cyclopropanamine (12.1 μL, 0.17 mmol, 1.1 equiv.) followed by DIPEA (41 μL, 0.24 mmol, 1.5 equiv.) and EDC (33.5 mg, 0.17 mmol, 1.1 equiv). The reaction mixture was allowed to reach r.t. and stirred overnight. The solvent was removed under reduced pressure and the residue directly purified by Combiflash chromatography (SiO2, c-Hexane/AcOEt) to afford (4aS,5S,10bS)-5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline-9-carboxylic acid (10 mg, 17%). The compound was prepared as hydrochloride salt following the method described in example 1.

Workup

  1. customto reach r.t.
  2. customThe solvent was removed under reduced pressure
  3. customthe residue directly purified by Combiflash chromatography (SiO2, c-Hexane/AcOEt)

Sources & evidence

ORD record
ord-cb93828469484036bb22be9e5a54051a
Source dataset
uspto-grants-2015_11
Patent number
US09193738B2

Reaction notes

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