Water → HCID 68567319, compound

HRID 1970031Notes

Reaction equation

HRID 1970031 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:12])[CH:10]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:13]1([NH2:16])[CH2:15][CH2:14]1.[BH4-].[Na+].O>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:12])[CH2:10][NH:16][CH:13]1[CH2:15][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 7015728tert-butyl N-((2S)-1-oxopropan-2-yl)carbamate

Product 1

HCID 68567319HCID 68567319, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

4.3 mL (14.3 mmol) of titanium isopropoxide and 1.9 g (5 mmol) of (S)-2-(tert-butoxycarbonylamino)-propionaldehyde (prepared according to the method described by Itaya, Taisuke et al., Tetrahedron Lett., 1986, 52(27), 6349-52) are added to a solution of 1.88 g (33 mmol) of cyclopropylamine in 10 mL of anhydrous methanol. The solution is stirred for 5 hours at room temperature then 227 mg (6 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 400 mg (17%) of (S)—N′-tert-butoxycarbonyl-N-cyclopropyl-propane-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-3e598c84445c455fb1217332348cc639
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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