4-Methoxybenzyl alcohol → HCID 86614063, compound

HRID 1727224Notes

Reaction equation

HRID 1727224 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]([CH3:12])[O:9][C@H:8]3[NH:13][C@H:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:15][C@@:7]3([OH:20])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26](CO)=[CH:25][CH:24]=1>C1(C)C=CC=CC=1.[O-]CC.[O-]CC.[O-]CC.[O-]CC.[Ti+4]>[Cl:1][C:2]1[C:11]2[N:10]([CH3:12])[O:9][C@H:8]3[NH:13][C@H:14]([C:16]([O:18][CH2:19][C:26]4[CH:29]=[CH:30][C:23]([O:22][CH3:21])=[CH:24][CH:25]=4)=[O:17])[CH2:15][C@@:7]3([OH:20])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 77384-Methoxybenzyl alcoholHCID 11381005HCID 11381005, compound

Product 1

HCID 86614063HCID 86614063, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 1140TolueneSolvent

Procedure

A stirred solution of methyl (2S,3aR,9bR)-6-chloro-9b-hydroxy-5-methyl-1, 2,3,3a,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylate (Preparation 118 25 g), para-methoxybenzyl alcohol (115 g) and titanium tetraethoxide (1.5 g) in toluene (300 ml) was heated at reflux for 1 hour. The reaction mixture was cooled, evaporated to a small volume and purified by flash column chromatography on silica gel eluting with a gradient of ethyl acetate:hexane (1:4 to 2:3) to give the product (29 g).

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureThe reaction mixture was cooled
  3. customevaporated to a small volume
  4. custompurified by flash column chromatography on silica gel eluting with a gradient of ethyl acetate:hexane (1:4 to 2:3)

Sources & evidence

ORD record
ord-3f9b9ea2758941e1b900f34f1708ec7c
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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