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

HRID 430689

反応式

HRID 430689 の反応式
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]

参加物

5

反応物 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

生成物 1

HCID 643455N-Boc-pyrrolidine収率 100.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (1.03 g, 7 mmol) was added to absolution 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.

後処理

  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

出典と根拠

ORDレコード
ord-d507fb58d8d54d0c92bbee971d94a725
出典データセット
uspto-grants-2001_11
特許番号
US06323223B1

関連ノート

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