Tetrahydrofuran → 1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

HRID 350716Notes

Reaction equation

HRID 350716 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.O1CCCC1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:20][S:21]([O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of tert-butyl 4-hydroxypiperidine-1-carboxylate (10 g) and tetrahydrofuran (100 mL) were successively added methanesulfonyl chloride (5.98 g) and triethylamme (5.53 g) at 0° C. The mixture was stirred at room temperature for 2 hrs., and the reaction mixture was diluted with ethyl acetate and washed successively with 1N aqueous sodium hydroxide solution, water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated to give tert-butyl 4-(methylsulfonyl)oxypiperidine-1-carboxylate as crystals. Recrystallization from ethyl acetate-hexane gave white prism crystals (13.2 g, yield 95%). melting point: 94–95° C.

Workup

  1. customat 0° C
  2. washwashed successively with 1N aqueous sodium hydroxide solution, water and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9baed365b7ab4c35b9ad0b78c4cb34f8
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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