Ethyl chloroformate → HCID 57888831, compound

HRID 1016165Notes

Reaction equation

HRID 1016165 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([OH:16])[CH2:13][CH2:12][NH:11][CH2:10][C:9]2([CH3:15])[CH3:14])=[CH:4][CH:3]=1.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([OH:16])[CH2:13][CH2:12][N:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:10][C:9]2([CH3:14])[CH3:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 66759036HCID 66759036, compound

Product 1

HCID 57888831HCID 57888831, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (R)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol (1.96 g, 8.18 mmol) in Pyridine (20 mL) was cooled to 0° C., then treated with the dropwise addition of ethyl chloroformate (0.942 mL, 9.81 mmol), causing a color change to orange. The mixture was allowed to come to room temperature and stirred over night. The reaction was concentrated in-vacuo, and the residue was taken up in ethyl acetate, washed 3× with 1M NaOH, 3× with 1M HCl, once with brine, dried over sodium sulfate, and concentrated in-vacuo to yield the title compound (2.4 g, 7.70 mmol, 94% yield). The residue was used as-is in the next step. MS (ESI+)=334, (M+Na)+.

Workup

  1. customto come to room temperature
  2. concentrationThe reaction was concentrated in-vacuo
  3. washwashed 3× with 1M NaOH, 3× with 1M HCl
  4. dry with materialonce with brine, dried over sodium sulfate
  5. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-b4f07f67c97d45079a7d15380cac2ddb
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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