Triethylamine → HCID 18656722, compound

HRID 1899325Notes

Reaction equation

HRID 1899325 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][C@H:16]([CH3:19])[CH2:17][OH:18])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl>[CH3:29][S:30]([O:18][CH2:17][C@@H:16]([CH3:19])[CH2:15][N:12]1[CH2:13][CH2:14][CH:9]([C:6]2[C:5]3[CH:20]=[CH:21][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:10][CH2:11]1)(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15391753(S)-(+)-3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-methyl1-propanol

Product 1

HCID 18656722HCID 18656722, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (S)-(+)-3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-methyl-1-propanol (8.8 g, 30 mmol), triethylamine (3.2 g, 32 mmol) in dichloromethane (DCM, 150 ml), methanesulfonyl chloride (4 g, 35 mmol) was added dropwise at 0° C. over 10 minutes. The mixture was stirred at room temperature for 1 hour, then concentrated. Triethylamine HCl salt was filtered off with a little DCM as solvent. The crude oil was purified with a flash chromatography column (SiO2, 90 g; eluted with DCM). The colorless oil thus purified weighed 5.28 g (47%) was used immediately in the following step.

Workup

  1. additionwas added dropwise at 0° C. over 10 minutes
  2. concentrationconcentrated
  3. filtrationTriethylamine HCl salt was filtered off with a little DCM as solvent
  4. customThe crude oil was purified with a flash chromatography column (SiO2, 90 g; eluted with DCM)
  5. customThe colorless oil thus purified

Sources & evidence

ORD record
ord-16fb0d6f11d44469bba35bc649ecdc16
Source dataset
uspto-grants-1996_11
Patent number
US05571803

Reaction notes

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