Diisopropylamine → N-(1-Hydroxy-1-phenylprop-2-yl)-N-methyl-2-butyl-3-cyclohexylpropionamide

HRID 1532880Notes

Reaction equation

HRID 1532880 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].C(NC(C)C)(C)C.[Cl-].[Li+].ICCCC.[OH:20][CH:21]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH:22]([N:24]([CH3:35])[C:25](=[O:34])[CH2:26][CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH3:23]>>[OH:20][CH:21]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH:22]([N:24]([CH3:35])[C:25](=[O:34])[CH:26]([CH2:2][CH2:3][CH2:4][CH3:5])[CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH3:23]

Participants

6

Reactant 5

HCID 7912DiisopropylamineHCID 10962Butyl iodideHCID 433294Lithium ChlorideHCID 22014104N-(1-Hydroxy-1-phenylprop-2-yl)-N-methyl-3-cyclohexylpropionamideHCID 178418339Butyllithium

Product 1

HCID 22014296N-(1-Hydroxy-1-phenylprop-2-yl)-N-methyl-2-butyl-3-cyclohexylpropionamideYield 53%

Procedure

A solution of 2.5M nBuLi in hexanes (5.8 mL, 14.5 mmol), diisopropylamine (2.0 mL, 14.5 mmol), lithium chloride (1.6 g, 39 mmol), iodobutane (130 μL, 6.4 mmol) and the product from Example 1315A (2.0 g, 6.4 mmol) were allowed to react in a manner similar to that described by A. G. Myers et al., Journal of the American Chemical Society 1994, 116: 9361-9362. The crude residue was chromatographed (silica gel; EtOAc/hexanes, 1:4) to afford the title compound as a yellow oil (1.2 g, 53%). MS (CI/NH3) m/z: 360 (M+H)+.

Workup

  1. customto react in a manner similar to
  2. customThe crude residue was chromatographed (silica gel; EtOAc/hexanes, 1:4)

Sources & evidence

ORD record
ord-6e05987e8b25483c86f021efc43c34e7
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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