Thiomorpholine → Sarsagenin

HRID 1865770Notes

Reaction equation

HRID 1865770 reaction equation
N1CCSCC1.[CH3:7][C@@H:8]1[CH2:36][O:35][C@@:11]2([O:15][C@H:14]3[CH2:16][C@H:17]4[C@@H:22]5[CH2:23][CH2:24][C@@H:25]6[CH2:30][C@@H:29]([OH:31])[CH2:28][CH2:27][C@:26]6([CH3:32])[C@H:21]5[CH2:20][CH2:19][C@:18]4([CH3:33])[C@H:13]3[C@@H:12]2[CH3:34])[CH2:10][CH2:9]1.C([O-])(=O)C=C>O1CCCC1>[CH3:7][C@@H:8]1[CH2:36][O:35][C@@:11]2([O:15][C@H:14]3[CH2:16][C@H:17]4[C@@H:22]5[CH2:23][CH2:24][C@@H:25]6[CH2:30][C@@H:29]([OH:31])[CH2:28][CH2:27][C@:26]6([CH3:32])[C@H:21]5[CH2:20][CH2:19][C@:18]4([CH3:33])[C@H:13]3[C@@H:12]2[CH3:34])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 86619921HCID 86619921, compound

Product 1

HCID 92095SarsageninYield 139.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.3 g of thiomorpholine (27) was added dropwise to a mixture of 47.1 g of sarsasapogenin acrylate (28) and 200 g. of tetrahydrofuran. The mixture was stirred at room temperature for 3 hours, after which tetrahydrofuran was distilled off. Subsequent purification by silica gel column chromatography gave 56.2 g of sarsasapogenin [3-(thiomorpholino)propionate] (Quencher 7). Yield 98%.

Workup

  1. distillationafter which tetrahydrofuran was distilled off
  2. customSubsequent purification by silica gel column chromatography

Sources & evidence

ORD record
ord-04d8465a273e4f0ca57607f174b981a5
Source dataset
uspto-grants-2009_12
Patent number
US07629108B2

Reaction notes

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