Triethylamine → HCID 86624148, compound

HRID 602464Notes

Reaction equation

HRID 602464 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][N:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH3:2].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([O:13][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:9][N:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67270690HCID 67270690, compound

Product 1

HCID 86624148HCID 86624148, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of tert-butyl trans-2-(3-ethoxy-3-oxopropyl)-5-hydroxypiperidine-1-carboxylate (625 mg, 2.07 mmol, step 3 of Example 5) and triethylamine (252 mg, 2.49 mmol) in dichloromethane (9.0 mL) was added methanesulfonyl chloride (285 g, 2.49 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 2 h and then stirred at room temperature for 20 h. The mixture was quenched with water (30 mL), extracted with dichloromethane (30 mL×4). The combined organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 790 mg (quant.) of the title compound as a yellow oil. The resulting residue was used for the next reaction without purification.

Workup

  1. stirringstirred at room temperature for 20 h
  2. customThe mixture was quenched with water (30 mL)
  3. extractionextracted with dichloromethane (30 mL×4)
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4ec07f9ab41a4e68951e5a0983f9431e
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

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