HCID 131729242, compound → HCID 59820023, compound

HRID 553563Notes

Reaction equation

HRID 553563 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][O:7][C@H:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([O:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=3)[O:19][C:20]=2[CH3:21])[CH2:9]1)=[N+]=[N-].[H][H]>CO.[Pd]>[CH3:21][C:20]1[O:19][C:18]([C:22]2[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=2)=[N:17][C:16]=1[CH2:15][O:14][C@H:10]1[CH2:11][CH2:12][CH2:13][C@@H:8]([O:7][CH2:6][CH2:5][CH2:4][NH2:1])[CH2:9]1

Participants

5

Reactant 2

HCID 131729242HCID 131729242, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59820023HCID 59820023, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

472 mg of ((1R,3S)-3-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]propyl 4-chloromethanesulfonate are dissolved in 3 ml of N-methylpyrrolidone, and 200 mg of sodium azide are added. The mixture is stirred at 60° C. for 3 h and, after cooling, taken up in 20 ml of ethyl acetate/20 ml with sat. NaCl solution. The organic phase is dried over sodium sulfate and the solvent is removed under reduced pressure. This gives 4-((1R,3S)-[3-(3-azidopropoxy)cyclohexyloxymethyl]-5-methyl-2-m-tolyloxazole as a colorless oil. C21H28N4O3 (384.48), MS (ESI): 385 (M+H+). The crude azide is taken up in 20 ml of methanol and hydrogenated with 50 mg of Pd/C 10% at a hydrogen atmosphere of 1 bar for 3 h. The catalyst is filtered off, giving (1R,3S)-3-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxy]propylamine as a colorless oil. C21H30N2O3 (358.48), MS (ESI): 359 (M+H+).

Workup

  1. filtrationThe catalyst is filtered off

Sources & evidence

ORD record
ord-fb29db4c7fd04a7db35bb16fa93f7c6e
Source dataset
uspto-grants-2011_11
Patent number
US08048901B2

Reaction notes

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