Water → HCID 57733422, compound

HRID 1920756Notes

Reaction equation

HRID 1920756 reaction equation
[C:1]1([C@@H:7]([NH:10][C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:23])[N:15]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]=2[CH2:30]Br)=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:32]#[N:33].[Na+].O.CCCCCCC>C1COCC1.CN(C=O)C>[C:1]1([C@@H:7]([NH:10][C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:23])[N:15]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]=2[CH2:30][C:32]#[N:33])=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8900HeptaneHCID 8929Sodium CyanideHCID 57733278HCID 57733278, compound

Product 1

HCID 57733422HCID 57733422, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromomethyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid ((S)-1-phenyl-propyl)-amide (83 mg, 0.174 mmol) in THF (1.5 ml, anhydrous) and DMF (1.5 ml, anhydrous) sodium cyanide (83 mg, excess) was added. After 5 min the obtained suspension was poured into water (50 ml) followed by addition of heptane (20 ml). The crude product was separated by filtration and purified by flash chromatography on SiO2 (5 g, 1:1 EA-heptane) to give 50 mg of colourless solid, yield 68%. LC-MS (m/z) 422.4 (MH+); tR=1.39. 1H NMR (250 MHz, DMSO-d6, T=343 K): 0.94 (t, 3H), 1.78 and 1.85 (two overlapping qui of ABX4, 2H, CH2 of Et), 3.45 and 3.54 (two d of AB, 2H, CH2CN), 4.98 (q, 1H), 7.22-7.44 (m, 8H), 7.53-7.64 (m, 4H), 7.72 (dt, 1H), 8.25 (dd, 1H), 9.05 (d, 1H).

Workup

  1. customThe crude product was separated by filtration
  2. custompurified by flash chromatography on SiO2 (5 g, 1:1 EA-heptane)

Sources & evidence

ORD record
ord-debd91a78eee41e6a9620c989807610e
Source dataset
uspto-grants-2012_05
Patent number
US08173639B2

Reaction notes

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