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

HRID 237492노트

반응식

HRID 237492 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a0d3ea4ab57740ebbd2ab55fa4e4a52b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642585B2

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