Triethylamine → HCID 54428075, compound

HRID 975684Notes

Reaction equation

HRID 975684 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[N:18][CH:19]=1)=[O:6])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:28]([CH3:27])(=[O:30])=[O:29])[CH2:9][C@H:8]1[CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[N:18][CH:19]=1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53777216HCID 53777216, compound

Product 1

HCID 54428075HCID 54428075, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen atmosphere to a solution of (2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-(pyrimidin-5-ylmethyl)pyrrolidine (21.0 g) in dichloromethane (105 ml) were added triethylamine (16.1 g) firstly and methanesulfonyl chloride (13.7 g) secondly at 5° to 10° C. After the reaction mixture was stirred for an hour at the same temperature, dichloromethane (50 ml) and ice-water (150 ml) were added thereto, and then the solution was stirred vigorously for twenty minutes. The organic layer was separated and washed with 1N-hydrochloric acid (100 ml), 1N-sodium hydroxide (200 ml), and brine (200 ml). The organic layer was dried over magnesium sulfate and evaporated under reduced pressure to give (2R,4R)-1-allyloxycarbonyl-4-methanesulfonyloxy-2-(pyrimidin-5-ylmethyl) pyrrolidine (25.2 g) as an oil.

Workup

  1. customsecondly at 5° to 10° C
  2. additionwere added
  3. customThe organic layer was separated
  4. washwashed with 1N-hydrochloric acid (100 ml), 1N-sodium hydroxide (200 ml), and brine (200 ml)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ad4a00284a6a47a08bce380d8a1a853a
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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