Acetic Acid → 1-Benzyl-4-[tert-butoxycarbonyl-(benzyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester

HRID 490573Notes

Reaction equation

HRID 490573 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH2:10])[CH2:7][N:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[O-]S([O-])(=O)=O.[Mg+2].[BH3-]C#N.[Na+].C[C:37]([OH:39])=[O:38]>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([N:10]([C:37]([O:39][C:12]([CH3:17])([CH3:13])[CH3:11])=[O:38])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7][N:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5003444Sodium cyanoborohydrideHCID 67547185HCID 67547185, compound

Product 1

HCID 675488151-Benzyl-4-[tert-butoxycarbonyl-(benzyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (10) and a benzaldehyde (unsubstituted or substituted by R1) in DCM are added MgSO4, AcOH, and then NaBH3CN. The reaction mixture is stirred overnight, and then diluted with DCM. The organic solution is washed with NaHCO3, dried and concentrated. The residue is dissolved in water, treated with (Boc)2O, and then stirred overnight. The reaction mixture is extracted with DCM, dried, and concentrated to give product 1-benzyl-4-[tert-butoxycarbonyl-(benzyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester (11).

Workup

  1. washThe organic solution is washed with NaHCO3
  2. customdried
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in water
  5. additiontreated with (Boc)2O
  6. stirringstirred overnight
  7. extractionThe reaction mixture is extracted with DCM
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2b82d28d78c64a06a469eeb4324a65d3
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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