Trimethylamine → HCID 86744039, compound

HRID 1534562Notes

Reaction equation

HRID 1534562 reaction equation
[ClH:1].[SH:2][C@@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]#[C:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:4]1=[O:17].CN(C)C.[CH3:22][S:23]COS([O-])(=O)=S.[OH-].[Na+]>ClCCl>[ClH:1].[CH3:22][S:23][S:2][C@@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]#[C:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[C:4]1=[O:17]

Participants

6

Reactant 4

HCID 1146TrimethylamineHCID 14798Sodium HydroxideHCID 86744040HCID 86744040, compoundHCID 86744041HCID 86744041, compound

Product 1

HCID 86744039HCID 86744039, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 430 mg of (R)-3-mercapto-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone hydrochloride in 20 ml of dichloromethane was cooled to 0° C. in an ice bath. Successively, 50 μl of trimethylamine and 0.5 ml of methylthiomethylthiosulfate were added and the resulting solution was stirred at room temperature for 30 minutes. A 1N sodium hydroxide solution (2 ml) was added and the resulting mixture was washed with saturated aqueous sodium chloride, dried and concentrated in vacuo. The residue was purified by chromatography (alumina) and the eluent containing the product band was acidified with an excess of 1.4N methanolic hydrogen chloride to give 0.41 g of the desired compound as a pale yellow oil, [α]D26 =+23° (methanol).

Workup

  1. washthe resulting mixture was washed with saturated aqueous sodium chloride
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography (alumina)
  5. additionthe eluent containing the product band

Sources & evidence

ORD record
ord-3916eb27971b40998586a3eae48eb8b7
Source dataset
uspto-grants-1992_02
Patent number
US05089518

Reaction notes

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