Pyrrolidine → 1′-(1,1-Dimethylethyl) 5′-methyl [1,3′-bipyrrolidine]-1′,5′-dicarboxylate

HRID 1012016Notes

Reaction equation

HRID 1012016 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C:7](=O)[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:4]1[N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH:7]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:8]1)=[O:17]

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 109884851-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate

Product 1

HCID 698173511′-(1,1-Dimethylethyl) 5′-methyl [1,3′-bipyrrolidine]-1′,5′-dicarboxylateYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-t-butoxycarbonyl-4-oxo-L-proline methyl ester (1.0 g, 4 mmol) (J. Org. Chem. 2001, 10, 3593), pyrrolidine (0.4 ml, 5 mmol), acetic add (0.3 ml, 5 mmol) in CH2Cl2 (20 ml) was added sodium triacetoxyborohydride (1.0 g, 5 mmol) and the mixture stirred for 2 h. After which time it was washed with saturated sodium hydrogen carbonate, dried (Na2SO4) and concentrated. Flash column chromatography (EtOAc:MeOH 95:5) afforded the title compound (1.0 g, 81%) as a yellow oil.

Workup

  1. washAfter which time it was washed with saturated sodium hydrogen carbonate
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a620527c7cf640c9be0760560488e1cc
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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