Triethylamine → HCID 18767822, compound

HRID 2300221Notes

Reaction equation

HRID 2300221 reaction equation
[CH2:1]1[CH:5]([OH:6])[CH2:4][NH:3][CH2:2]1.C(N(CC)CC)C.[CH2:14]([O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)[CH2:15][CH2:16][CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[CH2:14]([O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([N:3]2[CH2:2][CH2:1][CH:5]([OH:6])[CH2:4]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1)[CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 982104-HydroxypyrrolidineHCID 5179904-Butoxybenzenesulfonyl Chloride

Product 1

HCID 18767822HCID 18767822, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of DL-3-pyrrolidinol (0.87 g, 10 mmol) in dichloromethane (10 ml) was added triethylamine (1.21 g, 12 mmol) and 4-butoxybezenesulfonyl chloride (2.69 g, 10.5 mmol). The mixture was stirred at room temperature for 2 h. It was then treated with 10 ml of saturated sodium carbonate solution for 18 h. The mixture was diluted with water, and the organic solvents were evaporated. The resulting suspension was filtered, and the precipitate was washed with water and hexanes, and dried to give 2.89 g of an off-white solid; m.p. 83-84° C.; MS (ES) m/z 299.9 (MH+); HRMS (Cl) Calcd. for C14H22NO4S (MH+): 300.1269, Found: 300.1272.

Workup

  1. customthe organic solvents were evaporated
  2. filtrationThe resulting suspension was filtered
  3. washthe precipitate was washed with water and hexanes
  4. customdried

Sources & evidence

ORD record
ord-91e4a2120af04cf0b2856ec8e051f46a
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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