(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one → HCID 86693563, compound

HRID 575488Notes

Reaction equation

HRID 575488 reaction equation
ClC1C(C(OCC)=O)=[N:4]N2C=1CCOC1C=CC(I)=CC2=1.C([C@]1(O)CCN(C)C1=O)#C.[Cl:32][C:33]1[C:34]([C:57]([O:59]CC)=O)=[N:35][N:36]2[C:42]=1[CH2:41][CH2:40][O:39][C:38]1[CH:43]=[CH:44][C:45]([C:47]#[C:48][C@:49]3([OH:56])[CH2:53][CH2:52][N:51]([CH3:54])[C:50]3=[O:55])=[CH:46][C:37]2=1>>[Cl:32][C:33]1[C:34]([C:57]([NH2:4])=[O:59])=[N:35][N:36]2[C:42]=1[CH2:41][CH2:40][O:39][C:38]1[CH:43]=[CH:44][C:45]([C:47]#[C:48][C@:49]3([OH:56])[CH2:53][CH2:52][N:51]([CH3:54])[C:50]3=[O:55])=[CH:46][C:37]2=1

Participants

4

Reactant 3

HCID 86693296(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-oneHCID 86693564HCID 86693564, compoundHCID 89754566HCID 89754566, compound

Product 1

HCID 86693563HCID 86693563, compound

Procedure

Similar to as described in General Procedure G, racemic ethyl 3-chloro-9-iodo-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxylate was reacted with (R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one to give a diasteromeric mixture of (R)-ethyl 3-chloro-9-((3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2-carboxylate. Following aminolysis of the ethyl ester (similar to as described in General Procedure M) the titled compound was obtained after purification by prep HPLC.

Workup

  1. customto give

Sources & evidence

ORD record
ord-2fc8e9d7ddad42209e2bbd1482451c1e
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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