Ethanol → HCID 24966557, compound

HRID 1092330Notes

Reaction equation

HRID 1092330 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[N:11]1[CH2:15][CH:14]([CH:16]([CH3:18])[CH3:17])[NH:13][C:12]1=[O:19])[CH2:8]2.C(O)C>CCCCCCC>[CH:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH:2]1[N:11]1[CH2:15][C@@H:14]([CH:16]([CH3:17])[CH3:18])[NH:13][C:12]1=[O:19])[CH2:10]2.[CH:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH:2]1[N:11]1[CH2:15][C@H:14]([CH:16]([CH3:17])[CH3:18])[NH:13][C:12]1=[O:19])[CH2:10]2

Participants

5

Reactant 2

HCID 702EthanolHCID 24966556HCID 24966556, compound

Product 2

HCID 24966557HCID 24966557, compoundHCID 24966558HCID 24966558, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Racemic 1-adamantan-2-yl-4-isopropyl-imidazolidin-2-one (320 mg, example 51) was subjected to preparative HPLC (Column: Chiralpack AD; Eluent: 15% ethanol in heptane; Flow: 35 mL/min; Detection: UV 220 nm) to give (R)-1-adamantan-2-yl-4-isopropyl-imidazolidin-2-one (136 mg, tRet=45 min) and (S)-1-adamantan-2-yl-4-isopropyl-imidazolidin-2-one (115 mg, tRet=64 min). Absolute configurations are tentatively assigned.

Sources & evidence

ORD record
ord-459f8c16d7764bdb9d2bb8d7f476d80f
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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