Diisopropylethylamine → Tert-Butyl (1S,3S,4S,5S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-2-carboxylate

HRID 456724Notes

Reaction equation

HRID 456724 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14]([OH:16])=O)[C@@H:12]2[CH2:17][CH2:18][C@H:9]1[C@@H:10]([OH:20])[C@H:11]2[OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O[N:23]1[C:27]2[CH:28]=[CH:29][CH:30]=C[C:26]=2[N:25]=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.Cl.N1CCC[C@H]1C#N>CN(C)C=O>[C:26]([C@@H:27]1[CH2:28][CH2:29][CH2:30][N:23]1[C:14]([C@@H:13]1[C@@H:12]2[CH2:17][CH2:18][C@@H:9]([C@@H:10]([OH:20])[C@H:11]2[OH:19])[N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])=[O:16])#[N:25]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 44593801(2S)-Pyrrolidine-2-carbonitrile hydrochlorideHCID 69134634(1S,3S,4S,5S,6R)-2-(tert-Butoxycarbonyl)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylic Acid

Product 1

HCID 86598887Tert-Butyl (1S,3S,4S,5S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1S,3S,4S,5S,6R)-2-(tert-butoxycarbonyl)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylic acid obtained in Example 1-3 (500 mg) 1-hydroxybenzotriazole hydrate (415 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (493 mg) in dimethylformamide (10 mL), were added diisopropylethylamine and (2S)-2-pyrrolidinecarbonitrile hydrochloride with cooling on an ice bath. The reaction mixture was stirred at that temperature for 3 hrs.

Workup

  1. temperaturewith cooling on an ice bath

Sources & evidence

ORD record
ord-f4a85ca8b372443c83aae2e22ba635fc
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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