Benzaldehyde → (3R,4R)-di-tert-butyl 4-(benzyl(methyl)amino)pyrrolidine-1,3-dicarboxylate

HRID 456347Notes

Reaction equation

HRID 456347 reaction equation
[NH2:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4][C@H:3]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:29](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CO>[CH2:21]([N:1]([CH3:29])[C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4][C@H:3]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11483050(3R,4R)-di-tert-butyl 4-aminopyrrolidine-1,3-dicarboxylate

Product 1

HCID 68556735(3R,4R)-di-tert-butyl 4-(benzyl(methyl)amino)pyrrolidine-1,3-dicarboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of (3R,4R)-di-tert-butyl 4-aminopyrrolidine-1,3-dicarboxylate (Org. Biomol. Chem. 2004, 2, 2763-2776) (430 mg, 1.5 mmol) in dichloromethane/methanol (18 mL/2 mL) was added benzaldehyde (153 uL, 1.5 mmol) and sodium triacetoxyborohydride (1.89 g, 9.0 mmol). The mixture was stirred overnight and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried with magnesium sulfate, filtered and evaporated. The residue was purified on silica gel eluting with ethyl acetate/hexane (1:3) to give the title compound (495 mg, 88%). MS (ESI+) m/z=377 (M+H)+.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified on silica gel eluting with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-1495509d5774413d843b4414b9bc7342
Source dataset
uspto-grants-2013_07
Patent number
US08497275B2

Reaction notes

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