Water → Cyclopentanesulfonyl chloride

HRID 2399872Notes

Reaction equation

HRID 2399872 reaction equation
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].[CH:6]1([Mg]Cl)[CH2:10][CH2:9][CH2:8][CH2:7]1.O>CCCCCC.CCOCC>[CH:6]1([S:1]([Cl:5])(=[O:3])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 178478989HCID 178478989, compound

Product 1

HCID 3717197Cyclopentanesulfonyl chloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

Cyclopentanesulfonyl chloride was prepared according to the procedure of S. N. Bhattacharya, et. al., J. Chem. Soc. (C), 1265-1267 as follows. To a solution of 2.7 g (1.6 mL, 20 mmol) of sulfuryl chloride in 5 mL of hexane at 0° C. was added a solution of 5 mL (10 mmol) of 2 M cyclopentylmagnesium chloride in ether over a 15-min period. The reaction mixture was allowed to warm to room temperature and stir overnight. The mixture was recooled to 0° C. and a 5-mL portion of ether was added followed by a 10-mL portion of water. The layers were separated and the organic phase was washed with water, dried over sodium sulfate and concentrated to give 1.12 (70%) of cyclopentanesulfonyl chloride. This compound was used without further purification to prepare the title compound from the Cbz amine from Example 3 in a manner analogous to that of Example 5: 1H NMR (400 MHz, CDCl3) δ7.34-7.30 (m, 5H), 7.13 (s, 4H), 6.44 (br s, 1H), 5.07 (s, 2H), 4.74 (br, s, 1H), 3.50-3.39 (m, 3H), 2.76 (br t, 2H), 2.09-1.91 (m, 4H), 1.86-1.76 (m, 2H), 1.64-1.54 (m, 2H); FAB MS m/z 403 (M+1).

Workup

  1. customCyclopentanesulfonyl chloride was prepared
  2. customwas recooled to 0° C.
  3. customThe layers were separated
  4. washthe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f7cd81137f3e4b1e8d3efeb50900c1e8
Source dataset
uspto-grants-1995_09
Patent number
US05451677

Reaction notes

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