Triethylamine → (S)-tert-Butyl 2-(2-diazoacetyl)pyrrolidine-1-carboxylate

HRID 1735389Notes

Reaction equation

HRID 1735389 reaction equation
C(N(CC)CC)C.ClC(OCC)=O.[C:14]([O:18][C:19]([N:21]1[CH2:28][CH2:27][CH2:26][C@H:22]1[C:23]([OH:25])=O)=[O:20])([CH3:17])([CH3:16])[CH3:15].[N+:29](=[CH2:31])=[N-:30]>C1COCC1.C1(C)C=CC=CC=1>[C:14]([O:18][C:19]([N:21]1[CH2:28][CH2:27][CH2:26][C@H:22]1[C:23](=[O:25])[CH:31]=[N+:29]=[N-:30])=[O:20])([CH3:15])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9550DiazomethaneHCID 10928Ethyl chloroformateHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

Product 1

HCID 53788513(S)-tert-Butyl 2-(2-diazoacetyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (14.6 ml) and ethyl chloroformate (10.6 ml) were added to a solution of N-(tert-butoxycarbonyl)-L-proline (21.5 g) in THF (330 ml) at -20° C., and the mixture was stirred for 30 minutes. Then, diazomethane (0.6M, diethyl ether solution, 120 ml) was added, and the mixture was stirred overnight. Toluene was added to the reaction mixture, washed with a saturated aqueous solution of sodium bicarbonate and water in order, dried over anhydrous sodium sulfate, and concentrated to give the title compound (26.2 g).

Workup

  1. stirringthe mixture was stirred overnight
  2. washwashed with a saturated aqueous solution of sodium bicarbonate and water in order
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0a54de0bb6d1428f88a6072d4f6e4f3d
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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