Benzyl Alcohol → 5-(3-Chlorophenyl)-3-(1,2,3,4-tetrahydro-6,7-dihydroxynaphthalen-2-yl)-2-oxazolidinone

HRID 1721394Notes

Reaction equation

HRID 1721394 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[OH:4].C[O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24]C)[CH2:20][C:19](=O)[CH2:18][CH2:17]2.C([BH3-])#N.[Na+].C1([CH2:37][OH:38])C=CC=CC=1.B(Br)(Br)Br>CO.C(Cl)Cl.O>[Cl:11][C:7]1[CH:6]=[C:5]([CH:3]2[O:4][C:37](=[O:38])[N:1]([CH:18]3[CH2:19][CH2:20][C:21]4[C:16](=[CH:15][C:14]([OH:13])=[C:23]([OH:24])[CH:22]=4)[CH2:17]3)[CH2:2]2)[CH:10]=[CH:9][CH:8]=1

Participants

9

Reactant 5

HCID 244Benzyl AlcoholHCID 25134Boron tribromideHCID 6098446,7-Dimethoxy-2-tetraloneHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 5003444Sodium cyanoborohydride

Product 1

HCID 233581385-(3-Chlorophenyl)-3-(1,2,3,4-tetrahydro-6,7-dihydroxynaphthalen-2-yl)-2-oxazolidinone

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.83 g of 2-amino-1-(m-chlorophenyl)ethanol, 1.0 g of 6,7-dimethoxy-2-tetralone and 0.85 g of sodium cyanoborohydride in 25 ml of methyl alcohol is stirred at room temperature for 18 hours. The reaction mixture is poured into water and a product residue is isolated. This residue is purified by flash chromatography to give 0.80 g of 3-chloro-α- (1,2,3,4-tetrahydro-6,7-dimethoxy)naphthalen-2-yl)amino!methyl!benzenemethanol, which is in turn converted to 5-(3-chlorophenyl-3-(1,2,3,4-tetrahydro-6,7-dimethoxy)naphthalen-2-yl)-2-oxazolidinone. Subsequent reaction with boron tribromide in methylene chloride as in Example 1, Step A, gives 5-(3-chlorophenyl)-3-(1,2,3,4-tetrahydro-6,7-dihydroxynaphthalen-2-yl)-2-oxazolidinone as a solid, mp 195° C. (dec.).

Workup

  1. customa product residue is isolated
  2. customThis residue is purified by flash chromatography
  3. customto give 0.80 g of 3-chloro-α- (1,2,3,4-tetrahydro-6,7-dimethoxy)naphthalen-2-yl)amino

Sources & evidence

ORD record
ord-3b40c5660db747f5aa71e83447e6f388
Source dataset
uspto-grants-1996_04
Patent number
US05510376

Reaction notes

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