(3,5-Dimethoxyphenyl)methanamine → HCID 57786530, compound

HRID 253562Notes

Reaction equation

HRID 253562 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:9]2[CH2:11][O:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1)[CH2:25][NH2:26]>CC#N>[CH:1]1([CH2:7][C@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:9]([OH:10])[CH2:11][NH:26][CH2:25][C:24]2[CH:27]=[C:28]([O:30][CH3:31])[CH:29]=[C:22]([O:21][CH3:20])[CH:23]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 420973(3,5-Dimethoxyphenyl)methanamineHCID 9816868erythro-N-Boc-L-cyclohexylalanine epoxide

Product 1

HCID 57786530HCID 57786530, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl (S)-2-cyclohexyl-1-((S)-oxiran-2-yl)ethylcarbamate (67.3 mg, 0.25 mmol) in CH3CN (8 mL) was added 3,5-dimethoxybenzylamine (50 mg, 0.3 mmol) and the mixture was heated under reflux overnight. The solvent was removed in vacuo and the residue was purified by the preparative HPLC to give tert-butyl (2S,3R)-1-cyclohexyl-4-(3,5-dimethoxybenzylamino)-3-hydroxybutan-2-ylcarbamate (66.5 mg, 61%). 1H NMR: 0.82 (m, 1H), 0.95 (m, 1H), 1.10-1.48 (m, 6H), 1.42 (s, 9H), 1.65 (m, 4H), 1.80 (m, 1H), 2.67 (m, 2H), 3.46 (m, 1H), 3.64 (m, 1H), 3.72 (d, 2H), 3.79 (s, 6H), 6.35 (m, 1H). MS (E/Z): 437 (M+H+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by the preparative HPLC

Sources & evidence

ORD record
ord-7f3cb77c95fe4b12997ea5b6b6e7d5a4
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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