1-Amino-3-phenoxypropan-2-ol → HCID 15383952, compound

HRID 2294278Notes

Reaction equation

HRID 2294278 reaction equation
[O:1]([CH2:8][CH:9]([OH:12])[CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=[C:14]([CH3:31])[CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:19][CH:18]=1.C([BH3-])#N.[Na+]>CO>[O:1]([CH2:8][CH:9]([OH:12])[CH2:10][NH:11][CH:14]([CH3:31])[CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][CH:22]2[S:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:29][CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 27250731-Amino-3-phenoxypropan-2-olHCID 5003444Sodium cyanoborohydrideHCID 218321505-[4-(2-Oxopropoxy)benzyl]thiazolidine-2,4-dione

Product 1

HCID 15383952HCID 15383952, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A procedure similar to that described in Example 2 was repeated, except that 0.98 g of 3-phenoxy-2-hydroxypropylamine (prepared as described in Preparation 15), 3.39 g of 5-[4-(2-oxopropoxy)benzyl]thiazolidine-2,4-dione, 1.11 g of sodium cyanoborohydride and 60 ml of anhydrous methanol were used. The resulting crude product was purified by silica gel column chromatography (using a 10:1 by volume mixture of ethyl acetate and ethanol as the eluent) to give 1.92 g of the title compound, melting at 64° C. to 68° C.

Workup

  1. customThe resulting crude product was purified by silica gel column chromatography (
  2. additionby volume mixture of ethyl acetate and ethanol as the eluent)

Sources & evidence

ORD record
ord-a74dd311af0044deb1b3d5aa0db51873
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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