Sodium borohydride → 3-(4-Chloro-benzyl)-azetidine-1-carboxylic acid tert-butyl ester

HRID 1182098ノート

反応式

HRID 1182098 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)I)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 693587933-[(4-Chloro-phenyl)-iodo-methyl]-azetidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 693583843-(4-Chloro-benzyl)-azetidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A solution of 3-[(4-Chloro-phenyl)-iodo-methyl]-azetidine-1-carboxylic acid tert-butyl ester (58 g, 140 mmol) in dimethylsulphoxide (450 ml) is treated with sodium borohydride with cooling. The reaction mixture was stirred at room temperature for 20 hours, then quenched by the slow addition of water (1000 ml). The aqueous mixture is extracted into ethylacetate, and the ethylacetate phase washed with saturated brine, dried over magnesium sulphate and evaporated. The crude product is purified by flash chromatography using a biotage 75 column (eluant gradient isohexane:ethylacetate 9:1 to 85:15) to afford 3-(4-Chloro-benzyl)-azetidine-1-carboxylic acid tert-butyl ester. 1H NMR 400 MHz, CDCl3, δ 1.35 (9H), 2.70 (1H), 2.80 (2H), 3.55 (2H), 3.90 (2H), 6.97 (2H), 7.17 (2H).

後処理

  1. temperaturewith cooling
  2. customquenched by the slow addition of water (1000 ml)
  3. extractionThe aqueous mixture is extracted into ethylacetate
  4. washthe ethylacetate phase washed with saturated brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe crude product is purified by flash chromatography

出典と根拠

ORDレコード
ord-351c1662bfd34910b70ec4ca8300d864
出典データセット
uspto-grants-2007_10
特許番号
US07288537B2

反応ノート

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