Pyridine → HCID 66617741, compound

First step: To a stirred solution of commercially available (S)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester (2.38 g, 12 mmol) in CH2Cl2 (25 mL) at 0° C. were added pyridine (1.91 mL, 24 mmol) and methanesulfonyl chloride (0.92 mL, 12 mmol). Stirring was continued at RT overnight, the reaction was poured onto water and extracted with CH2Cl2. The combined organic phases were dried on Na2SO4 and concentrated under vacuo. The crude product was dissolved in CH2Cl2 (20 mL) and TFA (4 mL) was added. After 2 hours at RT, the volatiles were removed under vacuo, the crude was dissolved in CH2Cl2 and washed with aq. NaHCO3 (until pH=8). The organic phase was dried on Na2SO4 and concentrated under vacuo to yield 0.83 g (39%) of (s)-1-methanesulfonyl-2-methyl-piperazine as a light yellow oil.

1. additionthe reaction was poured onto water
2. extractionextracted with CH2Cl2
3. customThe combined organic phases were dried on Na2SO4
4. concentrationconcentrated under vacuo
5. dissolutionThe crude product was dissolved in CH2Cl2 (20 mL)
6. additionTFA (4 mL) was added
7. waitAfter 2 hours at RT
8. customthe volatiles were removed under vacuo
9. dissolutionthe crude was dissolved in CH2Cl2
10. washwashed with aq. NaHCO3 (until pH=8)
11. customThe organic phase was dried on Na2SO4
12. concentrationconcentrated under vacuo

ORD record

ord-f48bef12896841b5816fdad809f61e90

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07812021B2