2-Mercaptoethanol → HCID 21310355, compound

HRID 1837119Notes

Reaction equation

HRID 1837119 reaction equation
Br[CH2:2][C:3](=[O:26])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C@@H:11]([CH2:12][C@:13]([C:24]#[CH:25])([OH:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.[SH:27][CH2:28][CH2:29][OH:30].C(N(CC)CC)C.CCCCCC.CC(C)=O>C1COCC1>[C:24]([C@@:13]1([OH:23])[CH2:14][CH2:15][C@@:16]2([CH3:17])[C@H:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:18]2[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@H:7]3[CH2:6][CH2:5][C@@H:4]2[C:3](=[O:26])[CH2:2][S:27][CH2:28][CH2:29][OH:30])[CH2:12]1)#[CH:25]

Participants

6

Reactant 4

HCID 15672-MercaptoethanolHCID 8471TriethylamineHCID 21880519Acetone hexaneHCID 86754250HCID 86754250, compound

Product 1

HCID 21310355HCID 21310355, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 21-bromo-3β-ethynyl-3α-hydroxy-5β-pregnan-20-one (150 mg, 0.356 mmol), 2-mercaptoethanol (31 μL, 0.445 mmol), and triethylamine (62 μL, 0.445 mmol) in 5 mL of THF was stirred at room temperature overnight. The mixture was partitioned between EtOAc and water. The organic layer was washed with sat. aq. NaCl, dried with Na2SO4 and concentrated in vacuo resulting in 3β-ethynyl-3α-hydroxy-21-hydroxyethylthio-5β-pregnan-20-one (141 mg) as a white solid; mp 122-126° C.; TLC Rf (hexane:acetone 3:1)=0.11.

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. washThe organic layer was washed with sat. aq. NaCl
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated in vacuo
  5. customresulting in 3β-ethynyl-3α-hydroxy-21-hydroxyethylthio-5β-pregnan-20-one (141 mg) as a white solid

Sources & evidence

ORD record
ord-59fb1bbe0b0748f69d0b4fe31e51c977
Source dataset
uspto-grants-2004_08
Patent number
US06780853B1

Reaction notes

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