Isopropanol → Isopropyl 3-[4-(Diphenylmethyl)piperidin-1-yl]propanoate

HRID 2250412Notes

Reaction equation

HRID 2250412 reaction equation
[H-].[Na+].[C:3]1([CH:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18](OC)=[O:19])[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:28]([OH:31])([CH3:30])[CH3:29]>>[C:3]1([CH:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][C:18]([O:31][CH:28]([CH3:30])[CH3:29])=[O:19])[CH2:14][CH2:15]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 18441000HCID 18441000, compound

Product 1

HCID 18440998Isopropyl 3-[4-(Diphenylmethyl)piperidin-1-yl]propanoate

Procedure

A dispersion of NaH (˜20 mg of a 60% oil dispersion) was added to a solution of 13b (799 mg, 2.37 mmol) in isopropyl alcohol (10 mL). The resulting mixture was immediately stoppered tightly and stirred at RT for 2 h. The reaction mixture was evaporated to dryness and chromatographed over silica gel using 3:1 heptane/EtOAc to give 0.75 g of 13d as a colorless viscous oil. The structure was confirmed by 1H NMR. (Propanoate esters 13e and 13f were similarly prepared using isobutanol and cyclopentanol, respectively (as mentioned above, 13e was also prepared by the previous method using isobutyl acrylate).)

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customchromatographed over silica gel using 3:1 heptane/EtOAc

Sources & evidence

ORD record
ord-e17abc482c164609aa28559e44e3f085
Source dataset
uspto-grants-2008_01
Patent number
US07317026B2

Reaction notes

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