Triethylamine → (S)-tert-Butyl 3-((((benzyloxy)carbonyl)amino)methyl)pyrrolidine-1-carboxylate

HRID 639062Notes

Reaction equation

HRID 639062 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.C(N(CC)CC)C.[CH2:22]([O:29][C:30](ON1C(=O)CCC1=O)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[C:23]1([CH2:22][O:29][C:30]([NH:1][CH2:2][C@@H:3]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]2)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 1514454tert-Butyl (3S)-3-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 59254364(S)-tert-Butyl 3-((((benzyloxy)carbonyl)amino)methyl)pyrrolidine-1-carboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-3-(aminomethyl)-1-N-Boc-pyrrolidine (3.0 g, 14.98 mmole) in DMF (40 mL) was added triethylamine (2.5 mL, 17.94 mmole) and N-(benzyloxycarbonyloxy)succinimide (4.46 g, 17.90 mmole). After 18 hours, the reaction solution was concentrated under vacuum and redissolved in diethyl ether (250 mL). The organic solution was washed with H2O (2×150 mL), brine (100 mL) and dried over Na2SO4 and concentrated. The remaining residue was purified on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) to give the title compound (4.46 g, 91%) as a light yellow oil: LC-MS (ES) m/e 335 (M+H)+.

Workup

  1. concentrationthe reaction solution was concentrated under vacuum
  2. dissolutionredissolved in diethyl ether (250 mL)
  3. washThe organic solution was washed with H2O (2×150 mL), brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe remaining residue was purified on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH)

Sources & evidence

ORD record
ord-cea85dfa9917432fb09be13503a59872
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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