Potassium Iodide → HCID 54415333, compound

HRID 2399751Notes

Reaction equation

HRID 2399751 reaction equation
[C:1]1([C:7]([NH:20][CH2:21][CH:22]2[CH2:24][CH:23]2[CH2:25][OH:26])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[O:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[C:30]1[C:38]1[CH:45]=[CH:44][C:41]([CH2:42]Br)=[CH:40][CH:39]=1.[I-].[K+]>C1COCC1.CN(C=O)C>[C:1]1([C:7]([NH:20][CH2:21][C@@H:22]2[CH2:24][C@H:23]2[CH2:25][O:26][CH2:42][C:41]2[CH:44]=[CH:45][C:38]([C:30]3[O:29][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[N:31]=3)=[CH:39][CH:40]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 110335154-(Benzoxazol-2-yl)benzyl bromideHCID 19384402HCID 19384402, compound

Product 1

HCID 54415333HCID 54415333, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-triphenylmethylaminomethyl-1-hydroxymethylcyclopropane (0.338 g; 0.984 mmol) in 30 ml THF and 5 ml DMF is added sodium hydride (60%; 0.059 g; 1.48 mmol) followed by 4-(benzoxazol-2-yl)benzyl bromide (0.255 g; 0.886 mmol) and a pinch of potassium iodide. This is stirred overnight, quenched with water, concentrated in vacuo and flash chromatographed using hexane:ethyl-acetate; 7:1 to obtain trans-2-triphenylmethylaminomethyl-[4-(benzoxazol-2-yl)-benzyloxymethyl]cyclopropane as a pale yellow oil which is used directly in the next step.

Workup

  1. customquenched with water
  2. concentrationconcentrated in vacuo and flash
  3. customchromatographed

Sources & evidence

ORD record
ord-bbf3f3809e4e43489c64016ad1fdf932
Source dataset
uspto-grants-1995_09
Patent number
US05451596

Reaction notes

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