(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid → N-Boc-pyrrolidine

HRID 1610899Notes

Reaction equation

HRID 1610899 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[C:13]([N:20]1[CH2:27][CH2:26][CH2:25][C@@H:21]1C(O)=O)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].ClC1C=C(C=CC=1Cl)CN1CCNCC1>C(Cl)Cl>[C:16]([O:15][C:13]([N:20]1[CH2:27][CH2:26][CH2:25][CH2:21]1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27580741-(3,4-Dichlorobenzyl)piperazine

Product 1

HCID 643455N-Boc-pyrrolidineYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride(1.03 g, 7 mmol) was added to a solution of N-BOC-D-Proline (1.51 g, 7 mmol) in methylene chloride (12 ml) and the reaction mixture was stirred at room temperature. After 0.5 h, 3,4-dichlorobenzylpiperazine (1.32 g, 5.4 mmol) [prepared as described in Example 1] was added and the stirring was continued for 16 h. The reaction mixture was then quenched with water, basified with saturated sodium bicarbonate solution and extracted with ethyl acetate. The ethyl acetate layer was separated and washed with brine, dried over magnesium sulfate and concentrated. Flash chromatography with 30% acetone in dichloromethane as the eluant gave 2(R)-[4-(3,4-dichlorobenzyl)piperazin-1-ylcarbonyl]}-N-(tert-butoxycarbonyl) pyrrolidine (1.2 g) as an oil.

Workup

  1. waitthe stirring was continued for 16 h
  2. customThe reaction mixture was then quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe ethyl acetate layer was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-957cab2dc5c24c878155b94e7a60a712
Source dataset
uspto-grants-2006_01
Patent number
US06984637B2

Reaction notes

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