(-)-1-Cyclohexylethylamine → (2S,4S)-1-[[N-(4-[-N-[(1R)-1-cyclohexylethyl]amino]carbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

HRID 228064Notes

Reaction equation

HRID 228064 reaction equation
[C:1]([C:4]12[CH2:11][CH2:10][C:7]([NH:12][CH2:13][C:14]([N:16]3[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]3[C:22]#[N:23])=[O:15])([CH2:8][CH2:9]1)[CH2:6][CH2:5]2)(O)=[O:2].[CH:24]1([C@H:30]([NH2:32])[CH3:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>>[CH:24]1([C@H:30]([NH:32][C:1]([C:4]23[CH2:5][CH2:6][C:7]([NH:12][CH2:13][C:14]([N:16]4[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]4[C:22]#[N:23])=[O:15])([CH2:10][CH2:11]2)[CH2:8][CH2:9]3)=[O:2])[CH3:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 10997046(-)-1-CyclohexylethylamineHCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 57756775(2S,4S)-1-[[N-(4-[-N-[(1R)-1-cyclohexylethyl]amino]carbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Procedure

In a similar manner to Example 63, (2S,4S)-1-[[N-[4-carboxybicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (50.0 mg) and (1R)-1-cyclohexylethylamine (49.7 μL) were used to obtain (2S,4S)-1-[[N-(4-[-N-[(1R)-1-cyclohexylethyl]amino]carbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (29.9 mg).

Sources & evidence

ORD record
ord-a82aef1c5a0d4a0bbc204413011b3b4b
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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