Methylamine → 873221-70-6

HRID 1726947Notes

Reaction equation

HRID 1726947 reaction equation
[CH3:1][NH2:2].[CH3:3][C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1C=CC=CC=1>[CH3:3][C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:5][NH:2][CH3:1]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 24436Sodium Sulfate2×HCID 7015728tert-butyl N-((2S)-1-oxopropan-2-yl)carbamate

Product 1

HCID 24256598873221-70-6

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

6.00 ml methylamine solution (2 M in tetrahydrofuran) are added to 1.73 g tert.butyl ((S)-1-methyl-2-oxoethyl)-carbamate in 20 ml benzene with stirring at ambient temperature. Then 2.50 g anhydrous sodium sulphate are added and the reaction mixture is stirred overnight at ambient temperature. The sodium sulphate is suction filtered and washed again with benzene. The filtrate is evaporated down, taken up in 20 ml of methanol and combined with 397 mg sodium cyanoborohydride with stirring at ambient temperature. After 2.5 hours the reaction mixture is acidified by dropwise addition of approx. 20 ml 2 N citric acid and extracted with tert.-butylmethylether. The aqueous phase is made alkaline with 10 M sodium hydroxide solution and extracted with a methylene chloride/methanol mixture. The combined organic phases are dried over magnesium sulphate and evaporated down.

Workup

  1. stirringthe reaction mixture is stirred overnight at ambient temperature
  2. filtrationfiltered
  3. washwashed again with benzene
  4. customThe filtrate is evaporated down
  5. stirringwith stirring at ambient temperature
  6. additionAfter 2.5 hours the reaction mixture is acidified by dropwise addition of approx. 20 ml 2 N citric acid
  7. extractionextracted with tert.-butylmethylether
  8. extractionextracted with a methylene chloride/methanol mixture
  9. dry with materialThe combined organic phases are dried over magnesium sulphate
  10. customevaporated down

Sources & evidence

ORD record
ord-fd0fe8325b3c45adb33f988a93ed9471
Source dataset
uspto-grants-2009_02
Patent number
US07495002B2

Reaction notes

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