Triethylamine → HCID 86705001, compound

HRID 513023Notes

Reaction equation

HRID 513023 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][C@@H:11]([OH:13])[CH2:10][N:9]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][C@@H:11]([O:13][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:10][N:9]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66685055(2R,4R)-tert-butyl 2-(3-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 86705001HCID 86705001, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R,4R)-tert-butyl 2-(3-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylate (I-4A) (253 mg, 0.9 mmol) in DCM (6 mL) at 0° C. was added triethylamine (0.25 mL, 1.8 mmol) followed by dropwise addition of methanesulfonyl chloride (95 μL, 1.3 mmol). After stirring 2 hours at room temperature the reaction mixture was concentrated under reduced pressure and the resulting solid was extracted with Et2O (2×20 mL). The combined extracts were washed sequentially with 1% aqueous citric acid and brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford (2R,4R)-tert-butyl 2-(3-fluorophenyl)-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate (I-29) as a colorless oil. MS m/z 382.1 (M+23)+.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. extractionthe resulting solid was extracted with Et2O (2×20 mL)
  3. washThe combined extracts were washed sequentially with 1% aqueous citric acid and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ec99b17a3644d229f02fff8d7d3cf4e
Source dataset
uspto-grants-2015_08
Patent number
US09102671B2

Reaction notes

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