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

HRID 1436927Notes

Reaction equation

HRID 1436927 reaction equation
CS(Cl)(=O)=O.O[C@@H:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]1.C([N:21](CC)CC)C>ClCCl>[NH2:21][C@H:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (5. 26 mL, 68 mmol) was added dropwise over 5 minutes to a stirred solution of 1,1-dimethylethyl (3R)-3-hydroxypyrrolidine-1-carboxylate (10.6 g, 56.7 mmol) and triethylamine (11.8 mL, 85 mmol) in dichloromethane (250 mL) at −10° C. After stirring for 1 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 (25:75 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 (25:75 to 50:50)

Sources & evidence

ORD record
ord-95a1c167bef248b58d0d0d799bc2aa15
Source dataset
uspto-grants-2009_11
Patent number
US07619096B2

Reaction notes

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