Lithium borohydride → tert-Butyl 3-(hydroxymethyl)-3-methylazetidine-1-carboxylate

HRID 237492ノート

反応式

HRID 237492 の反応式
C[O:2][C:3]([C:5]1([CH3:16])[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6]1)=O.[BH4-].[Li+]>O1CCCC1.O>[C:12]([O:11][C:9]([N:7]1[CH2:8][C:5]([CH2:3][OH:2])([CH3:16])[CH2:6]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

参加物

5

反応物 2

HCID 4148881Lithium borohydrideHCID 574158901-Tert-butyl 3-methyl 3-methylazetidine-1,3-dicarboxylate

生成物 1

HCID 70700778tert-Butyl 3-(hydroxymethyl)-3-methylazetidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

3-Methyl-azetidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (WO2006/73361 A1, 2006) (1.1 g) is dissolved in 20 mL of tetrahydrofurane. Lithiumborohydride (16.8 mL of a 2 M solution in tetrahydrofurane) is added dropwise and the reaction mixture is stirred at room temperature overnight. The reaction mixture is diluted with water, washed with a saturated ammonium chloride water solution and the organic phase is separated, dried over sodium sulfate and concentrated under vacuum. The residue is chromatographed on silica gel (hexane/ethyl acetate 100:0→50:50) to give the title compound. Yield: 970 mg.

後処理

  1. washwashed with a saturated ammonium chloride water solution
  2. customthe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue is chromatographed on silica gel (hexane/ethyl acetate 100:0→50:50)

出典と根拠

ORDレコード
ord-a0d3ea4ab57740ebbd2ab55fa4e4a52b
出典データセット
uspto-grants-2014_02
特許番号
US08642585B2

反応ノート

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