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

HRID 1670624Notes

Reaction equation

HRID 1670624 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([O:19][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

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

Product 1

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add methanesulfonyl chloride (1.12 mol, 128.8 g) drop wise to a solution of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.74 mol, 150 g) and triethylamine (1.5 mol, 151.6 g) in dichloromethane (1 L) at 0° C. Upon complete addition, warm the reaction mixture to room temperature and stir for 16 h. Dilute the reaction mixture with dichloromethane, wash with saturated sodium bicarbonate solution and water. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate to obtain the title compound (192 g, 92%) as a brown solid. 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 9H), 1.78-1.85 (m, 2H), 1.93-1.98 (m, 2H), 3.03 (s, 3H), 3.26-3.32 (m, 2H), 3.68-3.71 (m, 2H), 4.85-4.90 (m 1H).

Workup

  1. additionUpon complete addition
  2. washwash with saturated sodium bicarbonate solution and water
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-5fbcb5037d664e73907f59c53a9b02f7
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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