Triphenylphosphine → HCID 59013845, compound

HRID 907551Notes

Reaction equation

HRID 907551 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([OH:20])=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:21][C:22]1[CH:27]=[C:26]([CH2:28]O)[CH:25]=[CH:24][N:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:19]([O:20][CH2:28][C:26]3[CH:25]=[CH:24][N:23]=[C:22]([F:21])[CH:27]=3)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 11332468(2-Fluoropyridin-4-yl)methanolHCID 178452262HCID 178452262, compound

Product 1

HCID 59013845HCID 59013845, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3′-hydroxy-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (304 mg, 1.08 mmol), 2-Fluoro-4-pyridinemethanol (138 mg, 1.08 mmol), and triphenylphosphine (286 mg, 1.09 mmol) in THF (5 mL) was added diethyl azidocarboxylate (210 mg, 1.21 mmol) dropwise. The resulting clear brown solution was stirred at room temperature for 16 h, then concentrated in vacuo. The crude solids were purified by flash chromatography (silica gel, 1:2 EtOAc:Hexanes). Product 3′-(2-fluoro-pyridin-4-ylmethoxy)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester was obtained as white solid (113 mg, 26.9% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude solids were purified by flash chromatography (silica gel, 1:2 EtOAc:Hexanes)

Sources & evidence

ORD record
ord-30b199b554c44bdbb6e72eecd288b844
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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