Triethylamine → HCID 57200596, compound

HRID 1375029Notes

Reaction equation

HRID 1375029 reaction equation
C(N(CC)CC)C.[CH2:8]([N:15]1[CH2:19][C@H:18]([OH:20])[CH2:17][C@H:16]1[C:21]([OH:24])([CH3:23])[CH3:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[CH2:8]([N:15]1[CH2:19][C@H:18]([O:20][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:17][C@H:16]1[C:21]([OH:24])([CH3:22])[CH3:23])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 56985716HCID 56985716, compound

Product 1

HCID 57200596HCID 57200596, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of triethylamine (4.32 ml) and (2S,4R)-1-benzyl-2-(1-hydroxy-1-methylethyl)-4-hydroxypyrrolidine (4.87 g) in dichloromethane (50 ml) was added methanesulfonyl chloride (2.4 ml) at 0° C. After stirring at room temperature for 4 hours, the mixture was quenched with water and extracted with ethyl acetate (×2). The combined extracts were washed with brine, dried over magnesium sulfate, evaporated under reduced pressure, and purified with column chromatography (silica gel, 500 ml, methanol:dichloromethane=4:96) to give (2S,4R)-1-benzyl-2-(1-hydroxy-1-methylethyl)-4-(methanesulfonyloxy)pyrrolidine (3.34 g) as a pale yellow solid.

Workup

  1. customthe mixture was quenched with water
  2. extractionextracted with ethyl acetate (×2)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. custompurified with column chromatography (silica gel, 500 ml, methanol:dichloromethane=4:96)

Sources & evidence

ORD record
ord-838117c0745840069494beead5d8c81d
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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