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Hydrochloric Acid → Boc-trans-4-(2-pyridinyl)-pyrrolidine-3-carboxylic acid

HRID 398398
Notes
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Reaction equation

HRID 398398 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C@H:10]([C:19]([O:21]CC)=[O:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C@H:10]([C:19]([OH:21])=[O:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 700249511-Tert-butyloxycarbonyl-trans-3-ethoxycarbonyl-4-(2-pyridyl)pyrrolidine

Product 1

HCID 2762196Boc-trans-4-(2-pyridinyl)-pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-tert-butyloxycarbonyl-trans-3-ethoxycarbonyl-4-(2-pyridyl)pyrrolidine from step 4 above (4.2 g, 13 mmol) in methanol (30 mL) was added aqueous NaOH (4.7 mL of a 4.0 N solution, 19 mmol). The resulting solution was stirred at ambient temperature for 48 h. The solution was acidified with aqueous HCl (3.1 mL of a 6.0 N solution, 19 mmol) and the solvents were removed in vacuo to give the title compound as an amorphous solid containing NaCl (HPLC RT=4.42 min, method A).

Workup

  1. customwere removed in vacuo

Sources & evidence

ORD record
ord-e69598bebfe5494db6ad677fc4ccc6ea
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06610692B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes