Triphenylphosphine → tert-Butyl 4-(5,6,7,8-tetrahydronaphtho[2,3-c][1,2,5]oxadiazol-6-yl)piperazine-1-carboxylate

HRID 1519513Notes

Reaction equation

HRID 1519513 reaction equation
[O-][N+:2]1[O:3][N:4]=[C:5]2[CH:14]=[C:13]3[C:8]([CH2:9][CH2:10][CH:11]([N:15]4[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]4)[CH2:12]3)=[CH:7][C:6]=12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[N:2]1[O:3][N:4]=[C:5]2[CH:14]=[C:13]3[C:8]([CH2:9][CH2:10][CH:11]([N:15]4[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]4)[CH2:12]3)=[CH:7][C:6]=12

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86694447tert-Butyl 4-(1-oxido-5,6,7,8-tetrahydronaphtho[2,3-c][1,2,5]oxadiazol-6-yl)piperazine-1-carboxylate

Product 1

HCID 86694448tert-Butyl 4-(5,6,7,8-tetrahydronaphtho[2,3-c][1,2,5]oxadiazol-6-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-Butyl 4-(1-oxido-5,6,7,8-tetrahydronaphtho[2,3-c][1,2,5]oxadiazol-6-yl)piperazine-1-carboxylate (100 mg, 0.27 mmol) and triphenyl phosphine (140 mg, 0.53 mmol) in THF (3 mL) was heated to 140° C. in a microwave reactor for 30 minutes. LC showed formation of the desired product, which was separated by reverse phase HPLC (water: Acetonitrile with 0.1% TFA). LC-MS (IE, m/z): 359 [M+1]+.

Sources & evidence

ORD record
ord-5d7b745fc12c4866b365aeebe0705d00
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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