2-Phenylethanol → HCID 13851365, compound

HRID 979165Notes

Reaction equation

HRID 979165 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:15][CH2:14][C@H:13]3[C@H:8]([CH2:9][N:10]([CH3:16])[CH2:11][CH2:12]3)[C:6]=2[CH:7]=1.[CH2:17](O)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:19]1([CH2:18][CH2:17][O:1][C:2]2[CH:3]=[CH:4][C:5]3[O:15][CH2:14][C@H:13]4[C@H:8]([CH2:9][N:10]([CH3:16])[CH2:11][CH2:12]4)[C:6]=3[CH:7]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 60542-PhenylethanolHCID 54295718HCID 54295718, compound

Product 1

HCID 13851365HCID 13851365, compound

Procedure

A mixture of 0.2 g (±)-[4aR*,10bS*]-1,3,4,4a,5,10b-hexahydro-9-hydroxy-2-methyl-2H-[1]benzopyrano[4,3-c]pyridine (m.p. of HCl salt 268°-269° ), 0.215 ml phenethyl alcohol and 0.3 g dicyclohexylcarboddiimide is heated under nitrogen for 18 hours at 130°. The cooled reaction mixture is flash chromatographed with CH2Cl2 /methanol (20:1) to yield the title compound; m.p. HCl salt 204°.

Workup

  1. temperatureis heated under nitrogen for 18 hours at 130°
  2. customThe cooled reaction mixture
  3. customchromatographed with CH2Cl2 /methanol (20:1)

Sources & evidence

ORD record
ord-f0c37b45ecd64e86a01f01433f02ff68
Source dataset
uspto-grants-1987_05
Patent number
US04666916

Reaction notes

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