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

HRID 1972086
Notes
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Reaction equation

HRID 1972086 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 Acetate
Solvent

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-563b03fee26d44aa83361b28f91688df
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08431575B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes