Tert-butyl 3-oxopyrrolidine-1-carboxylate → Benzyl 4-(pyrrolidin-3-yl)piperazine-1-carboxylate

HRID 1641934Notes

Reaction equation

HRID 1641934 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10](=O)[CH2:9]1)(OC(C)(C)C)=O.[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([BH3-])#N.[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(O)C>[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH2:26][CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 643495Benzyl piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21934646Benzyl 4-(pyrrolidin-3-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

1-N-BOC-3-pyrrolidinone (500 mg, 2.70 mmol), benzyl-1-piperazinecarboxylate (595 mg, 2.70 mmol) and titanium (IV) isopropoxide (960 mg, 3.37 mmol) are stirred under argon for 1 hour. Ethanol (3 ml) and sodium cyanoborohydride (113 mg, 1.80 mmol) are added and the reaction mixture stirred at room temperature over night. The compound is purified by reverse phase column chromatography (Isolute™ C18, 0-100% MeCN in water—0.1% TFA), followed by deprotection using trifluoroacetic acid (5 ml). The solvent is removed in vacuo and the compound is partitioned between chloroform and saturated NaHCO3(aq). The organics are dried (MgSO4), filtered and reduced in vacuo to yield the title compound.

Workup

  1. customThe compound is purified by reverse phase column chromatography (Isolute™ C18, 0-100% MeCN in water—0.1% TFA)
  2. customThe solvent is removed in vacuo
  3. customthe compound is partitioned between chloroform and saturated NaHCO3(aq)
  4. dry with materialThe organics are dried (MgSO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-a3df1d617e07412cb774c69e1972e03a
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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