Sodium Chloride → Tasimelteon

HRID 342105Notes

Reaction equation

HRID 342105 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([C@@H:15]3[CH2:17][C@H:16]3[CH2:18][NH2:19])[C:9]=2[CH2:8][CH2:7]1.[Na+].[Cl-]>>[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([C@@H:15]3[CH2:17][C@H:16]3[CH2:18][NH:19][C:1](=[O:4])[CH2:2][CH3:3])[C:9]=2[CH2:8][CH2:7]1

Participants

4

Reactant 3

HCID 5234Sodium ChlorideHCID 62324Propionyl chlorideHCID 15858319HCID 15858319, compound

Product 1

HCID 10220503Tasimelteon

Procedure

This compound was prepared similar to the above procedure using propionyl chloride and (-)-(trans)-2-(2,3-dihydrobenzofuran-4-yl)-cyclopropanemethanamine to give an oil that solidified upon standing to an off-white solid (61%, mp: 71°-72° C.). IR (NaCl Film): 3298, 1645, 1548, 1459, 1235 cm-1. [α]D25 : -17.3°; Anal. Calc'd for C15H19NO2 : C, 73.44; H, 7.87; N, 5.71; Found: C, 73.28; H, 7.68; N, 5.58.

Workup

  1. customThis compound was prepared similar to the above procedure
  2. customto give an oil that
  3. custom-17.3°

Sources & evidence

ORD record
ord-b267942a6efa48c58c6cbd5b174af137
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

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