Triethylamine → HCID 86594584, compound

HRID 1744167Notes

Reaction equation

HRID 1744167 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:15][C@@H:14]([CH3:16])[CH2:13][C@H:9]2[C:10]([OH:12])=O)[CH:5]=[CH:6][CH:7]=1.C1CN([P+](O[N:34]2N=[N:41][C:36]3C=CC=C[C:35]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.NCC#N.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:15][C@@H:14]([CH3:16])[CH2:13][C@H:9]2[C:10]([NH:41][CH2:36][C:35]#[N:34])=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 11491918Aminoacetonitrile hydrochlorideHCID 69152881HCID 69152881, compound

Product 1

HCID 86594584HCID 86594584, compound

Procedure

To (4S)-1-(3-bromophenyl)-4-methyl-L-proline (1.35 g, 4.75 mmol), PyBOP (2.72 g, 5.23 mmol), aminoacetonitrile hydrochloride (968 mg, 10.46 mmol) in dry DMW (30 mL) under dry nitrogen was added triethylamine (2.35 mL, 16.63 mmol) dropwise and the reaction was stirred overnight. Aqueous sat. NaHCO3 was added and the product extracted with Et2O (2×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (EtOAc/Hex, 35/75, then 4/6) to afford (4S)-1-(3-bromophenyl)-N-(cyanomethyl)-4-methyl-L-prolinamide.

Workup

  1. extractionthe product extracted with Et2O (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (EtOAc/Hex, 35/75

Sources & evidence

ORD record
ord-1cc2473377f542de980a22d184b72f27
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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