Triphenylphosphine → 1-Boc-4-(3-nitro-5-trifluoromethyl-phenoxy)-piperidine

HRID 1640126Notes

Reaction equation

HRID 1640126 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:14])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].O[CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1)[O:14][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 27562513-Hydroxy-5-nitrobenzotrifluorideHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 219596141-Boc-4-(3-nitro-5-trifluoromethyl-phenoxy)-piperidineYield 68.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-nitro-5-(trifluoromethyl)phenol (0.583 g, 2.82 mmol), tert-butyl 4-hydroxypiperidine-1-carboxylate (0.850 g, 4.22 mmol), PPh3 (1.11 g, 4.22 mmol), DIAD (0.67 mL, 4.22 rnmol), and benzene (8.7 mL) was allowed to stir at rt until reaction was judged to be complete. The reaction mixture was concentrated. The resulting off-white solid was purified by column chromatography to give tert-butyl 4-(3-nitro-5-(trifluoromethyl) -phenoxy)piperidine-1-carboxylate (0.750 g, 66%). 1H NMR (400 MHz, CD3OD) δ: 8.05-7.97 (m, 2H), 7.64 (s, 1H), 4.84-4.78 (m, 1H), 3.75-3.69 (m, 2H), 3.42-3.35 (m, 2H), 2.03-1.96 (m, 2H), 1.77-1.69 (m, 2H), and 1.46 (s, 9H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe resulting off-white solid was purified by column chromatography

Sources & evidence

ORD record
ord-7a46c27f9f6d434096f693e5b6bd3a0c
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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