Potassium hydroxide ethanol → 2-Amino-3-hydroxy-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one, (2R,3S)-

HRID 593270Notes

Reaction equation

HRID 593270 reaction equation
C1(C)C=CC(C([C@@](C(O)=O)(O)[C@@](C(C2C=CC(C)=CC=2)=O)(O)C(O)=O)=O)=CC=1.[NH2:29][C@H:30]([C@@H:38]([OH:45])[C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1)[C:31]([N:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:32].[OH-].[K+].C(O)C>CC(C)=O>[NH2:29][C@H:30]([C@@H:38]([OH:45])[C:39]1[CH:40]=[CH:41][N:42]=[CH:43][CH:44]=1)[C:31]([N:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:32]

Participants

4

Reactant 2

HCID 21946426Potassium hydroxide ethanolHCID 131734560(-)-(2R,3S)-2-Amino-3-hydroxy-3-pyridin-4-yl-1-pyrrolidin-1-yl-propan-1-one di-p-toluoyl-L-tartrate

Product 1

HCID 115359902-Amino-3-hydroxy-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one, (2R,3S)-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Step 3 contains three sub-steps. In step 3a, the (−)-(2R,3S)-2-Amino-3-hydroxy-3-pyridin-4-yl-1-pyrrolidin-1-yl-propan-1-one di-p-toluoyl-L-tartrate (ON-PYRAMIDE DPTL Tartrate) is treated with aqueous KOH/Ethanol and acetone to give the corresponding free base, i.e., (−)-(2R,3S)-2-Amino-3-hydroxy-3-pyridin-4-yl-1-pyrrolidin-1-yl-propan-1-one (ON-PYRAMID free base). Following this, there is a resin treatment with a sulfonic resin. Finally, tartrate formation takes place by treatment of the free base with L-tartaric acid in the presence of denatured ethanol. The detailed manufacturing process is given below:

Sources & evidence

ORD record
ord-b19c5cd52f4c4e6b9fc20bebcef258e8
Source dataset
uspto-grants-2016_01
Patent number
US09242935B2

Reaction notes

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