Water → HCID 59201550, compound

HRID 451721Notes

Reaction equation

HRID 451721 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)([O:12][CH2:13][CH2:14][OH:15])[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.[CH3:36][S:37](Cl)(=[O:39])=[O:38].O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:17]2)([O:12][CH2:13][CH2:14][O:15][S:37]([CH3:36])(=[O:39])=[O:38])[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59201346HCID 59201346, compound

Product 1

HCID 59201550HCID 59201550, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-hydroxyethoxy)butyl)piperidine-1-carboxylate (750 mg, 1.82 mmol) in dry CH2Cl2 (10 mL) was added Et3N (550 mg, 5.46 mmol) at −5-0° C. Then a solution of MsCl (270 mg, 2.37 mmol) in dry CH2Cl2 (5 mL) was added dropwise at the same temperature. After addition, it was allowed to warm to rt gradually. Upon completion of the reaction, water (20 mL) was added. The aqueous layer was extracted with CH2Cl2 (3×30 mL). The combined organic layers was washed with 10% citric acid, sat. NaHCO3 and brine, then dried over Na2SO4, filtered and concentrated to give (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-(methylsulfonyloxy)ethoxy)butyl)piperidine-1-carboxylate (900 mg, 99%), which was used in the next step without purification.

Workup

  1. additionAfter addition, it
  2. additionwas added
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×30 mL)
  4. washThe combined organic layers was washed with 10% citric acid, sat. NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8e58e23741064c2993b39e2e8f8f947e
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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