Methanesulfonyl chloride → HCID 86598344, compound

HRID 1270421Notes

Reaction equation

HRID 1270421 reaction equation
[CH2:1]([C@@H:8]1[CH2:13][N:12]2[CH2:14][C@@H:15]([OH:18])[CH2:16][CH2:17][C@@H:11]2[CH2:10][N:9]1[C:19]([C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>ClCCl>[CH2:1]([C@@H:8]1[CH2:13][N:12]2[CH2:14][C@@H:15]([O:18][S:45]([CH3:44])(=[O:47])=[O:46])[CH2:16][CH2:17][C@@H:11]2[CH2:10][N:9]1[C:19](=[O:20])[C:21]1[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[C:23]([C:31]([F:34])([F:32])[F:33])[CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 18449066HCID 18449066, compound

Product 1

HCID 86598344HCID 86598344, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (3R,7S,9aR)-(3-benzyl-7-hydroxy-octahydropyrido[1,2-a]pyrazin-2-yl)-(3,5-bis(trifluoromethyl)phenyl)-methanone (3.3 g, prepared analogous to example 3 steps 1–8) in dichloromethane (100 mL) was added diisopropylethylamine (2.4 mL) and methanesulfonyl chloride (0.8 mL), at 5° C. The resulting mixture was stirred at room temperature for 15 min. and concentrated in vacuo. The residue was purified by column chromatography (SiO2, CH2Cl2/MeOH 95:5) to afford methanesulfonic acid (3R,7S,9aR)-3-benzyl-2-(3,5-bis(trifluoromethyl)benzoyl)-octahydropyrido[1,2-a]pyrazin-7-yl ester (3.8 g). Rf 0.67 (CH2Cl2/MeOH 95:5) (intermediate 18).

Workup

  1. customat 5° C
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography (SiO2, CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-e0d5dd8f9b58461c994f41d79ebc6e19
Source dataset
uspto-grants-2007_04
Patent number
US07202238B2

Reaction notes

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