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

HRID 1176714Notes

Reaction equation

HRID 1176714 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>C1(C)C=CC=CC=1>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a cooled (5-10° C.) mixture of N-Boc-4-hydroxypiperidine (25.0 g, 124 mmol) and triethylamine (19.6 ml, 136 mmol) in toluene (120 ml) was added slowly methanesulfonyl chloride (10.6 ml, 136 mmol) via a syringe. The rate of the addition was kept at such rate that the temperature of the reaction mixture did not rise above 20° C. After completion of the addition, the temperature was kept at room temperature for one and a half hours. Water (50 ml) was added to the mixture, and an emulsion formed that was broken by the addition of 100 ml toluene. The aqueous layer was extracted with 100 ml toluene and the combined organic layers were dried over sodium sulfate, filtered, and evaporated to dryness, leaving a white solid residue identified as the product (30.5 g, 87%), and which was used as such in the next step.

Workup

  1. temperatureTo a cooled
  2. additionThe rate of the addition
  3. customdid not rise above 20° C
  4. additionAfter completion of the addition
  5. waitthe temperature was kept at room temperature for one and a half hours
  6. customan emulsion formed
  7. extractionThe aqueous layer was extracted with 100 ml toluene
  8. dry with materialthe combined organic layers were dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customleaving a white solid residue

Sources & evidence

ORD record
ord-0ace827015c04d2abe5774085d822b5f
Source dataset
uspto-grants-2010_11
Patent number
US07842819B2

Reaction notes

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