Triethylamine → HCID 67255486, compound

HRID 1192644Notes

Reaction equation

HRID 1192644 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[CH3:14][S:15](Cl)(=[O:17])=[O:16].C(N(CC)CC)C>C(Cl)Cl>[CH3:14][S:15]([NH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

Product 1

HCID 67255486HCID 67255486, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl(3S)-3-aminopyrrolidine-1-carboxylate (0.09 mL, 0.5 mmol) was combined with methanesulfonyl chloride (0.050 mL, 0.64 mmol) and triethylamine (0.22 mL, 1.6 mmol) in methylene chloride (2 mL) at room temperature and stirred for 2 hours. The reaction was diluted with dichloromethane, washed with water, dried over MgSO4, and concentrated. The residue was purified on silica gel (eluting with 0-10% methanol in dichloromethane) to give tert-butyl(3S)-3-[(methylsulfonyl)amino]pyrrolidine-1-carboxylate, LCMS [M+Na]+: m/z=287.1. The latter was treated with 4.57 M hydrogen chloride in 1,4-dioxane (1 mL, 4 mmol) at room temperature for 1 hour. The mixture was concentrated to give the desired product, which was used directly in the next step. LCMS calculated for C5H13N2O2S (M+H)+: m/z=165.1; Found: 165.1.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified on silica gel (eluting with 0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b7d065eca1a947a488a380c072b03afe
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

Loading…