Triethylamine → HCID 86656181, compound

HRID 1192635Notes

Reaction equation

HRID 1192635 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])(C)C)=[O:8])[CH2:3]1.[C:14](Cl)(=[O:17])[CH2:15][CH3:16].[CH2:19](N(CC)CC)[CH3:20]>C(Cl)Cl>[C:14]([NH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][CH2:13][CH2:19][CH3:20])=[O:8])[CH2:3]1)(=[O:17])[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

Product 1

HCID 86656181HCID 86656181, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl (3S)-3-aminopyrrolidine-1-carboxylate (0.09 mL, 0.5 mmol) was combined with propanoyl chloride (0.055 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, and dried over MgSO4, then concentrated. The resulting residue was purified on silica gel (eluting with 0 to 10% MeOH in dichloromethane) to give tent-butyl (3S)-3-(propionylamino)pyrrolidine-1-carboxylate, LCMS [M+Na] 265.2. The later 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 crude product (0.057 g) which was used directly in the next step. LCMS calculated for C7H15N2O (M+H)+: m/z=143.1; Found: 143.2.

Workup

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

Sources & evidence

ORD record
ord-7e6f3f395c9942c3abbc80dae351933e
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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