Hydrochloric Acid → HCID 86598266, compound

HRID 1726699Notes

Reaction equation

HRID 1726699 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C@H:15]3[CH2:20][CH2:19][CH:18]([C:21]([N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)=[O:22])[CH2:17][C@@H:16]3[C:28](OC)=[O:29])=[O:14])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([P+]([O:42][N:43]1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.Cl.C1(C2CCNCC=2)C=CC=CC=1.C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[OH:42][NH:43][C:28]([C@H:16]1[CH2:17][CH:18]([C:21]([N:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)=[O:22])[CH2:19][CH2:20][C@@H:15]1[C:13]([N:10]1[CH2:11][CH:12]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9]1)=[O:14])=[O:29]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 67304778HCID 67304778, compound

Product 1

HCID 86598266HCID 86598266, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Part 8. methyl(1S, 2S)-2-[(4-phenylpiperidin-1-yl)carbonyl]-5-(pyrrolidin-1-ylcarbonyl)cyclohexanecarboxylate: The product from Part 7 (0.112 g, 0.395 mmol) was dissolved in DMF (4.0 mL) and treated with BOP reagent (0.210 g, 0.474 mmol). After stirring for 10 min, the HCl salt of 4-phenyl-1,2,3,6-tetrahydropyridine (81 mg, 0.415 mmol) was added followed by N, N-diisopropylethylamine (206 μL, 1.18 mmol). The reaction mixture was stirred at rt overnight. It was poured into a saturated aq. NaHCO3 solution and extracted with EtOAc. The organic phase was washed with water (2×) and brine, dried over MgSO4, filtered and concentrated. The residue was flash chromatographed (silica, hexanes:EtOAc, 5:1 to 4:1 to 3:1) to provide the desired product (0.126 g, 79.7% yield). LCMS: m/z 425.2 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at rt overnight
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water (2×) and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed (silica, hexanes:EtOAc, 5:1 to 4:1 to 3:1)

Sources & evidence

ORD record
ord-2e34004fcdea4416bf6581e4c804378e
Source dataset
uspto-grants-2009_02
Patent number
US07491724B2

Reaction notes

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