Triphenylphosphine → HCID 58456714, compound

HRID 2036141Notes

Reaction equation

HRID 2036141 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2(F)[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:5]=[C:6]([F:9])[C:7]=1[OH:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=[O:46].[F:55][C:56]([F:71])([F:70])[C:57]1[N:61]=[C:60]([CH2:62][N:63]2[CH2:68][CH2:67][CH:66](O)[CH2:65][CH2:64]2)[O:59][N:58]=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:10]2([OH:46])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:5]=[C:6]([F:9])[C:7]=1[O:8][CH:66]1[CH2:67][CH2:68][N:63]([CH2:62][C:60]2[O:59][N:58]=[C:57]([C:56]([F:55])([F:70])[F:71])[N:61]=2)[CH2:64][CH2:65]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58456731HCID 58456731, compoundHCID 58456744HCID 58456744, compound

Product 1

HCID 58456714HCID 58456714, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 4-(3,5-difluoro-4-hydroxyphenyl)-4-fluoropiperidine-1-carboxylate D1g in dichloromethane (1 mL) is added to a mixture of triphenylphosphine (48 mg, 0.2 mmol) and diethyl azodicarboxylate (30 mg, 0.2 mmol) in dichloromethane (2 mL), followed by 1-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)piperidin-4-ol D1b (40 mg, 0.15 mmol). The mixture is stirred at room temperature overnight. Concentration and flash chromatography purification (hexanes/ethyl acetate gradient) yields tert-butyl 4-(3,5-difluoro-4-((1-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)piperidin-4-yl)oxy)phenyl)-4-hydroxypiperidine-1-carboxylate D1h as an oil. 19F-NMR (376 MHz, CDCl3) δ=−65.96 (3F), −126.00 (2F). LCMS calcd. for C25H32F5N4O5+ ([M+H]+): 563.2, found: 562.7.

Workup

  1. concentrationConcentration and flash chromatography purification (hexanes/ethyl acetate gradient)

Sources & evidence

ORD record
ord-d4faa1537b3e4edf901393cfe1d86997
Source dataset
uspto-grants-2013_11
Patent number
US08575168B2

Reaction notes

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