Triethylamine → HCID 22228407, compound

HRID 1795164Notes

Reaction equation

HRID 1795164 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][C:16]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)([CH2:19][OH:20])[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[CH2:14][CH2:15][C:16]([CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)([CH2:19][O:20][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:17][CH2:18]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11000987HCID 11000987, compound

Product 1

HCID 22228407HCID 22228407, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methane sulfonyl chloride (1.8 mL, 23.0 mmol) is added to a stirred solution of 4-cyclohexyl-4-hydroxymethylpiperidine-1-carboxylic acid tert-butyl ester, 3, (3.42 g, 11.48 mmol) and triethylamine (4.8 mL, 2.8 mmol) in dichloromethane (30 mL) at 0° C. The reaction mixture is then allowed to warm to room temperature and stir for 1 hour. The reaction is quenched with a saturated solution of NaHCO3 and the resulting mixture is extracted twice with dichloromethane (50 mL). The organic layers are combined, dried, filtered and concentrated in vacuo to yield the desired product in quantitative yield. The material is used for the next step without need for purification.

Workup

  1. customThe reaction is quenched with a saturated solution of NaHCO3
  2. extractionthe resulting mixture is extracted twice with dichloromethane (50 mL)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c44161145743428585398332d8ac9353
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

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