3-Methoxybenzylamine → tert-Butyl (1S,2R)-1-benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propylcarbamate

HRID 857258Notes

Reaction equation

HRID 857258 reaction equation
[O:1]1[CH2:3][CH:2]1[CH:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][NH2:26]>C(O)(C)C>[CH2:5]([C@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:2]([OH:1])[CH2:3][NH:26][CH2:25][C:24]1[CH:27]=[CH:28][CH:29]=[C:22]([O:21][CH3:20])[CH:23]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 211563-MethoxybenzylamineHCID 4571240tert-Butyl (1-(oxiran-2-yl)-2-phenylethyl)carbamate

Product 1

HCID 57512771tert-Butyl (1S,2R)-1-benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propylcarbamate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

tert-Butyl 1-(2-oxiranyl)-2-phenylethylcarbamate (V, commercially available, 20 g, 76 mmole) is dissolved in i-propanol (380 ml). To this mixture is added 3-methoxybenzyl amine (49 ml, 380 mmole). The reaction mixture is heated to reflux for 1 hr (when HPLC indicated complete reaction). The reaction mixture is concentrated under reduced pressure and the residue is treated with hexane (500 ml). The product is isolated by filtration. The mother liquors are concentrated under reduced pressure to give additional crude material which is partitioned between ethyl acetate (50 ml) and water (50 ml). The mixture is acidified with concentrated hydrochloric acid (to pH=4), the organic phase is separated and washed with water, saline, dried over sodium sulfate and then concentrated under reduced pressure to give additional title compound, M+H=401.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 1 hr
  3. custom(when HPLC indicated complete reaction)
  4. concentrationThe reaction mixture is concentrated under reduced pressure
  5. additionthe residue is treated with hexane (500 ml)
  6. customThe product is isolated by filtration
  7. concentrationThe mother liquors are concentrated under reduced pressure
  8. customto give additional crude material which
  9. customis partitioned between ethyl acetate (50 ml) and water (50 ml)
  10. customthe organic phase is separated
  11. washwashed with water, saline
  12. dry with materialdried over sodium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6a630062b84e421dbd26aa4bc2da6b65
Source dataset
uspto-grants-2006_12
Patent number
US07144897B2

Reaction notes

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