ChemicalBook CAS DataBase List (R)-N1,N1-diMethyl-4-(phenylthio)butane-1,3-diaMine

(R)-N1,N1-diMethyl-4-(phenylthio)butane-1,3-diaMine synthesis

7synthesis methods

Product Name:(R)-N1,N1-diMethyl-4-(phenylthio)butane-1,3-diaMine
CAS Number:870812-32-1
Molecular formula:C12H20N2S
Molecular Weight:224.37

870812-31-0 Synthesis

(R)-3-amino-N,N-dimethyl-4-(phenylthio)butanamide

870812-31-0
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(R)-N1,N1-diMethyl-4-(phenylthio)butane-1,3-diaMine

870812-32-1
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Yield:870812-32-1 55%

Reaction Conditions:

Stage #1: (3R)-3-amino-N,N-dimethyl-4-(phenylthio)butanamidewith dimethylsulfide borane complex in tetrahydrofuran at 20;
Stage #2: with hydrogenchloride in methanol;water;

Steps:

1.1M N-((3R)-3-amino-4-(phenylsulfanyl)butyl)-N,N-dimethylamine

N-((3R)-3-amino-4-(phenylsulfanyl)butyl)-N,N-dimethylamine A solution of EXAMPLE 1L (8.68 g, 36.5 mmol) in THF (200 mL) was treated with BH₃-dimethylsulfide (18.2 mL, 182.5 mmol) at room temperature, stirred overnight, treated slowly with methanol (20 mL), followed by 2N HCl (50 mL), stirred overnight, and concentrated. The resulting residue was purified by silica gel chromatography eluding with 5% 7N NH₃/CH₃OH in dichloromethane to give the desired product (4.50 g, 55%). MS (CI) m/e 224 (M+H)⁺.

References:

US2005/272744,2005,A1 Location in patent:Page/Page column 12