Triethylamine → HCID 18767822, compound

HRID 479950Notes

Reaction equation

HRID 479950 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 (CI) 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-0293423b352e4f80b79c0bf06c2f2d4a
Source dataset
uspto-grants-2003_11
Patent number
US06649603B2

Reaction notes

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