tert-Butyl 3-amino-3-(hydroxymethyl)pyrrolidine-1-carboxylate → HCID 67373624, compound

HRID 402080Notes

Reaction equation

HRID 402080 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([NH2:15])([CH2:13][OH:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC1C([O:23][C:24]([C:26]2[N:27]=[N:28][C:29]([CH2:45][CH2:46][CH2:47][CH3:48])=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]4)=[CH:34][CH:33]=3)[CH:31]=2)=O)=C(F)C(F)=C(F)C=1F>ClCCCl.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([NH:15][C:24]([C:26]2[N:27]=[N:28][C:29]([CH2:45][CH2:46][CH2:47][CH3:48])=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH:39]4[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]4)=[CH:34][CH:33]=3)[CH:31]=2)=[O:23])([CH2:13][OH:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 24730317tert-Butyl 3-amino-3-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 866578236-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid pentafluorophenyl ester

Product 1

HCID 67373624HCID 67373624, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-amino-3-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.0 mmol, 0.21 g) in anhydrous DCE (2 mL), 6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid pentafluorophenyl ester (Example 93, 0.5 mmol, 0.26 g) and TEA (0.5 mL) was stirred at room temperature for 3 h. The reaction mixture was diluted with ethyl acetate (10 mL) and washed with NaOH (0.5 M) solution, water, and brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography using ethyl acetate:hexanes (7:3) to provide 3-{[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carbonyl]-amino}-3-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. washwashed with NaOH (0.5 M) solution, water, and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-aa843b8e50ec41aca2f1cee0794d6e27
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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