Triethylamine → 1-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acid

HRID 1283846

反応式

HRID 1283846 の反応式
C(N1CCC(C(O)=O)C1)C1C=CC=CC=1.[NH:16]1[CH2:20][CH2:19][CH:18]([C:21]([OH:23])=[O:22])[CH2:17]1.C(N(CC)CC)C.[C:31]([O:35][C:36](N=[N+]=[N-])=[O:37])([CH3:34])([CH3:33])[CH3:32].[N-]=[N+]=[N-]>C(O)(=O)C.[Pd].CN(C=O)C.O>[C:31]([O:35][C:36]([N:16]1[CH2:20][CH2:19][CH:18]([C:21]([OH:23])=[O:22])[CH2:17]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]

参加物

9

反応物 5

HCID 8471TriethylamineHCID 33558AzideHCID 61256Carbonazidic acid, 1,1-dimethylethyl esterHCID 30346453-Pyrrolidinecarboxylic acidHCID 46173481-benzylpyrrolidine-3-carboxylic Acid

生成物 1

HCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acid

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒HCID 21962138N,N-Dimethylformamide--water (1/1)溶媒

実験手順

A solution of 205 g. (1 mol.) of N-benzylpyrrolidine-3-carboxylic acid (CA, 64 14173d) is dissolved in glacial acetic acid (1 l.) and hydrogenated in the presence of 40 g. of 10% palladium on charcoal until no more starting material is detected by TLC. The catalyst is filtered off and the filtrate is concentrated to dryness in vacuo. The residual 3-pyrrolidine carboxylic acid is dissolved in a mixture of DMF-H2O (2:1) (2 liters), triethylamine (1 mol.), t-butoxycarbonyl azide (1.5 mol.) is added and the mixture is stirred at room temperature for two days. Periodically the pH is tested with pH paper, and after twenty-four hours more azide (0.5 mol.) is added. The solvent is concentrated in vacuo to remove the DMF, the aqueous phase is acidified with citric acid (to pH 2-3) and extracted with ethyl acetate. The organic phase is concentrated to dryness in vacuo to yield the product 1-(t-butyloxycarbonyl)-3-pyrrolidinecarboxylic acid.

後処理

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated to dryness in vacuo
  3. additionis added
  4. concentrationThe solvent is concentrated in vacuo
  5. customto remove the DMF
  6. extractionextracted with ethyl acetate
  7. concentrationThe organic phase is concentrated to dryness in vacuo

出典と根拠

ORDレコード
ord-dd959544468b462a8ddaf8774f1400b1
出典データセット
uspto-grants-1976_08
特許番号
US03976660

関連ノート

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