Ethanol → (6S)-6-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1466017Notes

Reaction equation

HRID 1466017 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([N:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][C:14]1=[O:26])[CH2:7][CH2:6]2)#[N:2].C(O)C>CCCCCCC>[O:26]=[C:14]1[CH2:15][NH:16][CH2:17][CH2:18][N:13]1[C@H:8]1[CH2:7][CH2:6][C:5]2[CH:4]=[C:3]([C:1]#[N:2])[CH:12]=[CH:11][C:10]=2[CH2:9]1

Participants

4

Reactant 2

HCID 702EthanolHCID 131732668tert-Butyl 4-(6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)-3-oxopiperazine-1-carboxylate

Product 1

HCID 89524982(6S)-6-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

tert-Butyl 4-(6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)-3-oxopiperazine-1-carboxylate was resolved on the OD column with 20% Ethanol and Heptane. The faster eluting isomer was tentatively assigned as the (S)-isomer, and the slower isomer as the (R)-isomer. Treating the (S)-isomer with 4N HCl gave rise to (6S)-6-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile, and the (R)-isomer gave rise to (6R)-6-(2-oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile.

Workup

  1. washThe faster eluting isomer
  2. additionTreating the (S)-isomer with 4N HCl

Sources & evidence

ORD record
ord-7add44f00a7342899114b63651e08e78
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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