tert-Butyl 3-(aminomethyl)-3-methylpyrrolidine-1-carboxylate → HCID 86716578, compound

HRID 715500Notes

Reaction equation

HRID 715500 reaction equation
[NH2:1][CH2:2][C:3]1([CH3:15])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.[O:16]1[C@:18]2([CH2:23][CH2:22][CH2:21][C@H:20]([CH2:24][N:25]3[C:29]4[CH:30]=[C:31]([C:34]#[N:35])[CH:32]=[CH:33][C:28]=4[N:27]=[CH:26]3)[CH2:19]2)[CH2:17]1>C(O)(C)C>[C:34]([C:31]1[CH:32]=[CH:33][C:28]2[N:27]=[CH:26][N:25]([CH2:24][C@H:20]3[CH2:21][CH2:22][CH2:23][C@:18]([CH2:17][NH:1][CH2:2][C:3]4([CH3:15])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]4)([OH:16])[CH2:19]3)[C:29]=2[CH:30]=1)#[N:35]

Participants

4

Reactant 2

HCID 57073985tert-Butyl 3-(aminomethyl)-3-methylpyrrolidine-1-carboxylateHCID 86716579HCID 86716579, compound

Product 1

HCID 86716578HCID 86716578, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 1,1-dimethylethyl 3-(aminomethyl)-3-methyl-1-pyrrolidinecarboxylate (0.677 g, 3.16 mmol) and 1-[(3S,5S)-1-oxaspiro[2.5]oct-5-ylmethyl]-1H-benzimidazole-6-carbonitrile (0.844 g, 3.16 mmol) in isopropanol (5 mL) was heated at 102° C. overnight. The reaction mixture was concentrated and purified via silica gel chromatography (ISCO, 40 g silica gel column. Solvent A: DCM; B: MeOH; 0-10% B: 15 min; 10% B: 10 min) to give 1,1-dimethylethyl 3-{[({(1S,3S)-3-[(6-cyano-1H-benzimidazol-1-yl)methyl]-1-hydroxycyclohexaneyl}methyl)amino]methyl}-3-methyl-1-pyrrolidinecarboxylate (950 mg, 62.4% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified via silica gel chromatography (ISCO, 40 g silica gel column. Solvent A: DCM; B: MeOH; 0-10% B: 15 min; 10% B: 10 min)

Sources & evidence

ORD record
ord-dc2235a046bf4c1ba17cfa7c2d786535
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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