Triethylamine → HCID 22940602, compound

HRID 1977047Notes

Reaction equation

HRID 1977047 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]2[CH2:14][C@H:15]([CH2:18][OH:19])[CH2:16][CH2:17][C@H:10]2[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].[OH-].[Na+]>C(Cl)Cl.O>[C:1]([N:8]1[CH2:13][CH2:12][N:11]2[CH2:14][C@H:15]([CH2:18][O:19][S:28]([CH3:27])(=[O:30])=[O:29])[CH2:16][CH2:17][C@H:10]2[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 22882696HCID 22882696, compound

Product 1

HCID 22940602HCID 22940602, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6.0 g (22 mmol) of (7R,9aS)-2-BOC-7-hydroxymethyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine (WO 93/25552) and 3.41 mL (24.4 mmol) of triethylamine in 225 mL of dry methylene chloride was chilled to 0° C., and treated with 1.80 mL (23.3 mmol) of methansulfonyl chloride in 75 mL of methylene chloride. After stirring 1 h, water was added and the pH adjusted to 12 with 15% sodium hydroxide. The layers were separated and the aqueous phase extracted with methylene chloride. The combined organic phase was dried (magnesium sulfate), filtered and evaporated to give 7.73 g (100%) of (7R,9aS)-2-BOC-7-(methanesulfonyloxy)methyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase extracted with methylene chloride
  3. dry with materialThe combined organic phase was dried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-0cf23f838b5c40de97d490d44790b22a
Source dataset
uspto-grants-2001_05
Patent number
US06231833B1

Reaction notes

Loading…