Triethylamine → tert-butyl (3S)-3-aminopiperidine-1-carboxylate

HRID 2113602Notes

Reaction equation

HRID 2113602 reaction equation
CS(Cl)(=O)=O.O[C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1.C([N:22](CC)CC)C>ClCCl>[NH2:22][C@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1514398(R)-1-Boc-3-hydroxypiperidine

Product 1

HCID 1501975tert-butyl (3S)-3-aminopiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (9.56 mL, 124 mmol) was added dropwise over 10 minutes to a stirred solution of 1,1-dimethylethyl (3R)-3-hydroxypiperidine-1-carboxylate (20.7 g, 103 mmol) and triethylamine (21.5 mL, 154 mmol) in dichloromethane (300 mL) at 0° C. After stirring for 3 hour at 0° C., the reaction was quenched by addition of water. The organic phase was washed with brine, dried (MgSO4), filtered and evaporated in vacuo to give an oil. This was purified by flash chromatography on silica, eluting with ethyl acetate/cyclohexane (20:80 to 50:50), to give the title compound as an oil.

Workup

  1. customthe reaction was quenched by addition of water
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give an oil
  7. customThis was purified by flash chromatography on silica
  8. washeluting with ethyl acetate/cyclohexane (20:80 to 50:50)

Sources & evidence

ORD record
ord-7858c37462804c8fa89cbaf7bc52e010
Source dataset
uspto-grants-2008_10
Patent number
US07432280B2

Reaction notes

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