Triphenylphosphine → HCID 69673273, compound

HRID 1426365Notes

Reaction equation

HRID 1426365 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.O[C:49]1[N:54]=[C:53]([C:55]([F:58])([F:57])[F:56])[N:52]=[C:51]([CH2:59][C:60]([O:62][CH3:63])=[O:61])[CH:50]=1>O1CCCC1>[CH3:63][O:62][C:60](=[O:61])[CH2:59][C:51]1[N:52]=[C:53]([C:55]([F:57])([F:58])[F:56])[N:54]=[C:49]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH:50]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 178499535HCID 178499535, compound

Product 1

HCID 69673273HCID 69673273, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl 4-hydroxypiperidine-1-carboxylate (213 mg, 1.06 mmol, Aldrich) in tetrahydrofuran (2.0 mL) was added Triphenylphosphine (0.284 g, 1.08 mmol), followed by diisopropyl azodicarboxylate (0.215 mL, 1.09 mmol). After 10 minutes, methyl [6-hydroxy-2-(trifluoromethyl)pyrimidin-4-yl]acetate (0.20 g, 0.85 mmol, from Step 1) was added. The reaction was stirred for 1 hour and solvent was removed in vacuo. Flash chromatography on a 40 g silica gel cartridge, eluting with a gradient from 0-20%) EtOAc in hexanes afforded product as a viscous oil (127 mg, 25%). LCMS (M+H)+: 420.0.

Workup

  1. customsolvent was removed in vacuo
  2. washFlash chromatography on a 40 g silica gel cartridge, eluting with a gradient from 0-20%) EtOAc in hexanes afforded product as a viscous oil (127 mg, 25%)

Sources & evidence

ORD record
ord-640b07e38e2349bbb4be34727b68c310
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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