Methanol → HCID 86627533, compound

HRID 1970033Notes

Reaction equation

HRID 1970033 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][CH:11]=O)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:13]([NH2:16])[C:14]#[CH:15].CO.[BH4-].[Na+]>O1CCCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].O>[C:1]([O:5][C:6]([N:8]([CH3:9])[CH2:10][CH2:11][NH:16][CH2:13][C:14]#[CH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 887MethanolHCID 239041PropargylamineHCID 4311764Sodium borohydrideHCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamate

Product 1

HCID 86627533HCID 86627533, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.7 mL (9.1 mmol) of titanium isopropoxide and 1.2 g (7 mmol) of (tert-butoxycarbonyl-methyl-amino)-acetaldehyde (prepared according to the method described by Kato, Shiro et al., J. Chem. Soc. Perkin Trans. 1, 1997, 21, 3219-26) are added to a solution of 1.16 g (21 mmol) of propargylamine in 50 mL of anhydrous tetrahydrofuran. The solution is stirred for 5 hours at room temperature then 5 mL of anhydrous methanol and 317 mg (8.4 mmol) of sodium borohydride is added. Stirring is continued for a further 2 hours then 2 mL of water is added. The reaction mixture is filtered then the solvents are evaporated. The residue is purified by chromatography on silica (eluent dichloromethane/methanol 98/2) to give 550 mg (37%) of N-tert-butoxycarbonyl-N-methyl-N′-prop-2-ynyl-ethane-1,2-diamine in the form of a colourless oil.

Workup

  1. stirringStirring
  2. waitis continued for a further 2 hours
  3. filtrationThe reaction mixture is filtered
  4. customthe solvents are evaporated
  5. customThe residue is purified by chromatography on silica (eluent dichloromethane/methanol 98/2)

Sources & evidence

ORD record
ord-fe3be202cd4c426a971b64c8257a7e59
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

Loading…