Methyl iodide → N-(3-(1-Admantyl)-4-isopropoxyphenethyl)-2,2,2-trifluoro-N-methyl-acetamide

HRID 710452Notes

Reaction equation

HRID 710452 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:23]=[CH:24][C:25]=3[O:26][CH:27]([CH3:29])[CH3:28])[CH2:14][CH2:15][NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:30]I>C1COCC1>[C:1]12([C:11]3[CH:12]=[C:13]([CH:23]=[CH:24][C:25]=3[O:26][CH:27]([CH3:29])[CH3:28])[CH2:14][CH2:15][N:16]([CH3:30])[C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 87126503N-(3-(1Admantyl)-4-isopropoxyphenethyl)-2,2,2-trifluoro-acetamide

Product 1

HCID 87126604N-(3-(1-Admantyl)-4-isopropoxyphenethyl)-2,2,2-trifluoro-N-methyl-acetamideYield 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step D (0.25 g, 0.61 mmol) in anhydrous THF (5 ml) 60% NaH in mineral oil (0.03 g, 0.75 mmol) was added at 0° C. and the mixture was stirred for 2 h. To it MeI (0.23 ml) was added and the resulting mixture was stirred for additional 3 h. The mixture was passed trough Celite bead and washed with CH2Cl2 (10 ml). The combined filtrates were evaporated to dryness to give the title product (0.22 g; 85.3%). 1H-NMR (CDCl3) 1.36 (d, 6H, J=6 Hz); 1.75 (s, 6H); 2.04 (s, 3H); 2.09 (s, 6H); 2.8 (tr, 2H, J=7.7 Hz); 2.96 (s, 3H); 3.59 (tr, 2H, J=6.02 Hz); 4.58-4.63 (m, 1H); 6.76 (d, 1H, J=8.32 Hz); 6.91-7.01 (m, 2H).

Workup

  1. stirringthe resulting mixture was stirred for additional 3 h
  2. washwashed with CH2Cl2 (10 ml)
  3. customThe combined filtrates were evaporated to dryness

Sources & evidence

ORD record
ord-ccdea7c65ae44bc58092ba59cb179bbf
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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