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

HRID 411506Notes

Reaction equation

HRID 411506 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([N:13]1[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].CCN(CC)CC>C(Cl)Cl>[C:6]([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:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

5

Reactant 3

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

Product 1

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulphonyl chloride (20 ml, 0.26 mol) in CH2Cl2 (200 ml) was added dropwise over 15 min to a solution of N-BOC 4-piperidinol (46 g, 0.23 mol) and Et3N (64 ml, 0.46 mol) in CH2Cl2 (430 ml) cooled below 7° C. using a salt/ice bath. After addition was complete, stirring was continued for 15 min. The reaction was warmed to room temperature and quenched with 1N HCl (200 ml). The organic phase was washed with further 1N HCl (200 ml), brine (50 ml), 1N NaOH (100 ml), dried (MgSO4) and evaporated to give 60 g (94% yield) of product as a colourless solid. δH (360 MHz, CDCl3) 1.46 (9H, s), 1.75-1.85 (2H, m), 1.90-2.00 (2H, m), 3.0 (3H, s), 3.25-3.35 (2H, m), 3.65-3.75 (2H, m), 4.85-4.95 (1H, m).

Workup

  1. temperaturecooled below 7° C.
  2. additionAfter addition
  3. customquenched with 1N HCl (200 ml)
  4. washThe organic phase was washed with further 1N HCl (200 ml), brine (50 ml), 1N NaOH (100 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-e16904b24cdf4c2cb28460ac5706e49c
Source dataset
uspto-grants-2003_05
Patent number
US06559166B1

Reaction notes

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