Methanol → Tert-butyl 3-(2-aminoethoxy)-3-(3-chlorophenyl)propyl(methyl)carbamate

HRID 426036Notes

Reaction equation

HRID 426036 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([O:20][CH2:21][C:22]#[N:23])[CH2:9][CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[CH:6][CH:7]=1.S(C)C.CO>C1COCC1>[NH2:23][CH2:22][CH2:21][O:20][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH2:9][CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 66704520Tert-butyl 3-(3-chlorophenyl)-3-(cyanomethoxy)propyl(methyl)carbamate

Product 1

HCID 59364336Tert-butyl 3-(2-aminoethoxy)-3-(3-chlorophenyl)propyl(methyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 3-(3-chlorophenyl)-3-(cyanomethoxy)propyl(methyl)carbamate (3 g, 8.9 mmol) in THF (50 mL) was heated to reflux and BH3.Me2S was added drop wise. The reaction mixture was heated to reflux overnight. MeOH was added to the mixture at −15° C. The solution was removed in vacuo to give the crude product, which was used for the next step without purification.

Workup

  1. temperatureto reflux
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux overnight
  4. customThe solution was removed in vacuo

Sources & evidence

ORD record
ord-8420366f243e4aa0a4e97666bff7a0ee
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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