Water → HCID 86749049, compound

HRID 2210700Notes

Reaction equation

HRID 2210700 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][C@H:15]2[CH2:20][CH2:19][C:18](=[O:21])[N:17](CC3C=CC(OC)=CC=3)[C@H:16]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O.[N+]([O-])([O-])=O.[NH4+].[Ce]>C(#N)C>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([CH2:13][O:14][C@H:15]2[CH2:20][CH2:19][C:18](=[O:21])[NH:17][C@H:16]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:4]=[C:3]([C:2]([F:1])([F:37])[F:38])[CH:8]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 57418452Ammonium cerium-nitrateHCID 86749050HCID 86749050, compound

Product 1

HCID 86749049HCID 86749049, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

cis-3-((3,5-Bis(trifluoromethyl)phenyl)methyloxy)-6-keto-1-(4-methoxybenzyl)-2-phenyl piperidine (0.17 g, Example 27) was dissolved in acetonitrile (3 ml) and water (1 ml) then cooled to 0° C. and cerium ammonium nitrate (173 mg) was added. The mixture was stirred at 23° C. for 18h, then poured into water (10 ml) and extracted with ethyl acetate (3×15 ml). The combined organic extracts were washed with brine (1×10 ml) then dried (MgSO4) and concentrated to leave a pale yellow oil. Purification on silica gel (hexanes/ethyl acetate 1:1 then ethyl acetate then methanol/ethyl acetate 1:9) provided cis-3-((3,5-bis(trifluoromethyl)phenyl)methyloxy)-6-keto-2-phenyl piperidine as an oil. 1H NMR (360 MHz, CDCl3) δ7.72 (1H, s), 7.44 (2H, s), 7.37 (5H, m), 5.86 (1H, s), 4.75 (1H, d, J=3.2 Hz), 4.52 (1H, d, J=12.5 Hz), 4.14 (1H, d, J=12.5 Hz), 3.98 (1H, m), 2.65 (1H, ddd, J=6.4, 12.2, 18.2 Hz), 2.48 (1H, m), 2.30 (1H, m), 2.06 (1H, m). m/z (CI+) 418 (MH).

Workup

  1. extractionextracted with ethyl acetate (3×15 ml)
  2. washThe combined organic extracts were washed with brine (1×10 ml)
  3. dry with materialthen dried (MgSO4)
  4. concentrationconcentrated
  5. customto leave a pale yellow oil
  6. customPurification on silica gel (hexanes/ethyl acetate 1:1

Sources & evidence

ORD record
ord-17da68d8e60c4e62971fdcc8efbdcf5d
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

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