Diisopropylethylamine → (3R,4R)-di-tert-butyl 4-(benzyloxycarbonylamino)pyrrolidine-1,3-dicarboxylate

HRID 456346Notes

Reaction equation

HRID 456346 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].CCN(C(C)C)C(C)C.[C:30](C1CC(=O)NC1=O)([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>CN(C)C=O>[CH2:33]([O:32][C:30]([NH: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])=[O:31])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11483050(3R,4R)-di-tert-butyl 4-aminopyrrolidine-1,3-dicarboxylateHCID 21878410(Carbobenzoxy)succinimide

Product 1

HCID 68552708(3R,4R)-di-tert-butyl 4-(benzyloxycarbonylamino)pyrrolidine-1,3-dicarboxylateYield 105.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3R,4R)-di-tert-butyl 4-aminopyrrolidine-1,3-dicarboxylate (Org. Biomol. Chem. 2004, 2, 2763-2776) (765 mg, 2.67 mmol) and Hunig's base (465 uL, 2.67 mmol) in N,N-dimethylformamide (5 mL) was added Cbz succinimide (665 mg, 2.67 mmol). The mixture was stirred for 3 hours and partitioned between EtOAc and water. The organic layer was washed repeatedly with brine, dried (Na2SO4) and concentrated to a clear oil (1.18 g, quantitative yield). MS (DCI/NH4) m/z=438 (M+NH4)+.

Workup

  1. custompartitioned between EtOAc and water
  2. washThe organic layer was washed repeatedly with brine
  3. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-f4db5497f1164c88a8c345e63abe2c49
Source dataset
uspto-grants-2013_07
Patent number
US08497275B2

Reaction notes

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