1-(t-Butoxycarbonyl)-4-(3-iodo-2,2-dimethylpropyl)-piperidine → HCID 21180662, compound

HRID 1386750Notes

Reaction equation

HRID 1386750 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([CH3:19])([CH3:18])[CH2:16]I)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:20]1([Mg]Br)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCOCC.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Ni]Cl.[Fe]>[C:20]1([CH2:16][C:15]([CH3:18])([CH3:19])[CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 211806341-(t-Butoxycarbonyl)-4-(3-iodo-2,2-dimethylpropyl)-piperidineHCID 178418255HCID 178418255, compound

Product 1

HCID 21180662HCID 21180662, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 178477753HCID 178477753, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 26 mg (0.07 mmol) of 1-(t-butoxycarbonyl)-4-(3-iodo-2,2-dimethylpropyl)piperidine (from EXAMPLE 98, Step H) and 2 mg (0.007 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]nickel (II) chloride in ether (5 mL) at reflux was treated with phenylmagnesium bromide (0.13 mL of 3.0 M solution in ether). The resulting mixture was heated at reflux for 12 h, cooled and quenched with H2O and sat'd NaCl. The mixture was extracted 3× with CH2Cl2 and the combined organic layers were dried over Na2SO4, filtered and the filtrate concentrated. The residue was purified by column chomatography on 10 g of silica using a gradient of 0-5% MeOH/CH2Cl2 (v/v), then 10% MeOH/CH2Cl2+2% NH401H (v/v), to give 9 mg (56%) of the title compound: 1H NMR (500 MHz) δ 0.89 (s, 6H), 1.18-1.27 (4H), 1.52-1.59 (m, 1H), 1.71 (d, J=12.3,21).2.46 (bs, 1H) 2.52 (s, 2H), 2.65 (t, J=11.9, 2H). 3.06 (d,J=12.2, 2H), 7.13 (d, J=7.3, 2H), 7.22 (t, J=7.1, 11H), 7.28 (t, J=6.7, 2H).

Workup

  1. temperatureat reflux
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux for 12 h
  4. temperaturecooled
  5. customquenched with H2O
  6. extractionThe mixture was extracted 3× with CH2Cl2
  7. dry with materialthe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated
  10. customThe residue was purified by column chomatography on 10 g of silica using a gradient of 0-5% MeOH/CH2Cl2 (v/v)

Sources & evidence

ORD record
ord-21f8b13d913a4357b7a897aad62bed51
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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