(3-Ethylphenyl)methanamine → tert-butyl (1S,2R)-1-[3-(benzyloxy)-5-fluorobenzyl]-3-[(3-ethylbenzyl)amino]-2-hydroxypropylcarbamate

HRID 14327Notes

Reaction equation

HRID 14327 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([CH:25]1[CH2:27][O:26]1)[CH2:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:29]([C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH2:34][NH2:35])[CH3:30]>C(O)(C)C>[CH2:18]([O:17][C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([F:16])[CH:13]=1)[CH2:9][C@H:8]([NH:7][C:6](=[O:28])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[C@H:25]([OH:26])[CH2:27][NH:35][CH2:34][C:33]1[CH:36]=[CH:37][CH:38]=[C:31]([CH2:29][CH3:30])[CH:32]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 11446358(3-Ethylphenyl)methanamineHCID 72459586[2-(3-Benzyloxy-5-fluoro-phenyl)-1-oxiranyl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 58802266tert-butyl (1S,2R)-1-[3-(benzyloxy)-5-fluorobenzyl]-3-[(3-ethylbenzyl)amino]-2-hydroxypropylcarbamateYield 96%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

[2-(3-Benzyloxy-5-fluoro-phenyl)-1-oxiranyl-ethyl]-carbamic acid tert-butyl ester (3.33 g, 8.59 mmol) and m-ethyl benzylamine (2.32 g, 17.19 mmol) were dissolved in isopropyl alcohol (80 ml) and brought to reflux for 2 h. Reaction mixture was then concentrated in vacuo to remove isopropyl alcohol. Dissolved yellow liquid in ethyl acetate (30 ml), then washed with 1N HCl (3×100 ml). Aqueous layers were combined then extracted with ethyl acetate (2×100 ml). Organic layers were washed with 10% sodium bicarbonate (aq., 3×100 ml), followed by a brine wash. Organic layer was dried over sodium sulfate, filtered, then concentrated in vacuo, yielding the product (4.31 g). (ES+: 523.9)

Workup

  1. temperatureto reflux for 2 h
  2. customReaction mixture
  3. concentrationwas then concentrated in vacuo
  4. customto remove isopropyl alcohol
  5. dissolutionDissolved yellow liquid in ethyl acetate (30 ml)
  6. washwashed with 1N HCl (3×100 ml)
  7. extractionAqueous layers were combined then extracted with ethyl acetate (2×100 ml)
  8. washOrganic layers were washed with 10% sodium bicarbonate (aq., 3×100 ml)
  9. washwash
  10. dry with materialOrganic layer was dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4cc253dac45e4ed6a93f3ea4d708dc6a
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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