HCID 86641456, compound → HCID 68524524, compound

HRID 1189972Notes

Reaction equation

HRID 1189972 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[CH:10]=[C:11]([CH:15]3[O:17][CH:16]3[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)=O>[CH:1]1([CH2:7][NH:8][C:9]2[CH:10]=[C:11]([CH2:15][CH:16]([OH:17])[CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 86641456HCID 86641456, compound

Product 1

HCID 68524524HCID 68524524, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of tert-butyl (3-(3-(cyclohexylmethylamino)phenyl)oxiran-2-yl)methylcarbamate, HCOOH.Et3N complex (5:2), Pd/C (10% wt) in absolute EtOH is degassed by applying vacuum/argon 3 times. The reaction mixture is stirred at room temperature until no starting material is seen by TLC, then concentrated under reduced pressure. Purification by flash chromatography (EtOAc—hexanes gradient) gives tert-butyl 3-(3-(cyclohexylmethylamino)phenyl)-2-hydroxypropylcarbamate.

Workup

  1. customEt3N complex (5:2), Pd/C (10% wt) in absolute EtOH is degassed
  2. concentrationconcentrated under reduced pressure
  3. customPurification by flash chromatography (EtOAc—hexanes gradient)

Sources & evidence

ORD record
ord-a021fbc4a96a4506be789f4ec8458604
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

Loading…