N-Methylbenzeneethanamine → HCID 71656890, compound

HRID 2278176Notes

Reaction equation

HRID 2278176 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[CH3:13][O:14][C:15](=[O:22])[CH:16]([C:18]([F:21])([F:20])[F:19])[OH:17].C(N(CC)C(C)C)(C)C.[CH3:32][NH:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl>[F:19][C:18]([F:21])([F:20])[CH:16]([O:17][C:5](=[O:11])[N:33]([CH3:32])[CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:15]([O:14][CH3:13])=[O:22]

Participants

6

Reactant 4

HCID 11503N-MethylbenzeneethanamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 2760118methyl 3,3,3-trifluoro-dl-lactate

Product 1

HCID 71656890HCID 71656890, compoundYield 210.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of triphosgene (20 mg, 0.07 mmol) in CH2Cl2 (5.0 mL) was added methyl-3,3,3-trifluoro-DL-lactate (36 mg, 0.23 mmol) followed by N,N-diisopropylethylamine (120 μL, 0.69 mmol). After 2 h, N-methyl phenethylamine (31 mg, 0.23 mmol) was added as a solution in CH2Cl2 (2 mL) and stirred for another 2 h. The mixture was concentrated under reduced pressure and purified directly by SiO2 flash chromatography (25% EtOAc/hexanes) to provide the titled compound (47 mg, 64%): 1H NMR 500 MHz (CDCl3) δ 7.34-7.28 (m, 2H), 7.25-7.18 (m, 3H), 5.51-5.42 (m, 1H), 3.87 (s, 1.8H), 3.86 (s, 1.2H), 3.60-3.46 (m, 2H), 2.96-2.90 (m, 2.5H), 2.90-2.83 (m, 2.5H); HRMS m/z calc'd for [M+H]+ C14H16F3NO4: 320.1104. found 320.1109.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompurified directly by SiO2 flash chromatography (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f9ecb4a6851f42c6826c9cb54d88630a
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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