Ammonia → 9-Mercapto-3-(2-(3-furyl)ethyl)-spiro[5.5]undecane

HRID 1757222Notes

Reaction equation

HRID 1757222 reaction equation
C([S:4][CH:5]1[CH2:22][CH2:21][C:8]2([CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]3[CH:20]=[CH:19][O:18][CH:17]=3)[CH2:10][CH2:9]2)[CH2:7][CH2:6]1)(=O)C.[H][H].N>CO.O1CCCC1>[SH:4][CH:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][C:16]3[CH:20]=[CH:19][O:18][CH:17]=3)[CH2:12][CH2:13]2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 152348629-Acetylthio-3-(2-(3-furyl)ethyl)-spiro[5.5]undecaneHCID 178418361HCID 178418361, compound

Product 1

HCID 152348549-Mercapto-3-(2-(3-furyl)ethyl)-spiro[5.5]undecaneYield 92.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 0.100 g of 9-acetylthio-3-(2-(3-furyl)ethyl)-spiro[5.5]undecane in 5 ml of methanol/tetrahydrofuran 3/1, was saturated with hydrogen and successively with gaseous ammonia and kept on standing for 3 hrs at room temperature. The mixture was evaporated to dryness and purified by flash chromatography (SiO2 ; n-hexane/diethylether 80/20) to give 0.080 g of 9-mercapto-3-(2-(3-furyl)ethyl)-spiro[5.5]undecane as a white sticky oil. TLC: Rf=0.38 (SiO2 plates, n-hexane/diethylether 80/20). 1H-NMR (300 MHz, CDCl3, ppm from TMS): 7.36 (1H, m), 7.20 (1H, m), 6.27 (1H, m), 2.90 (1H, m), 2.48 (2H, t), 1.90-0.85 (19H, m).

Workup

  1. customThe mixture was evaporated to dryness
  2. custompurified by flash chromatography (SiO2 ; n-hexane/diethylether 80/20)

Sources & evidence

ORD record
ord-7e0cf30f7a7547488daefa1e4dd247bb
Source dataset
uspto-grants-1995_08
Patent number
US05444082

Reaction notes

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