Borane;tetrahydrofuran → (S)-tert-butyl 5-(hydroxymethyl)-6-azaspiro[2.5]octane-6-carboxylate

HRID 536584

반응식

HRID 536584 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:11]2([CH2:13][CH2:12]2)[CH2:10][C@H:9]1[C:16](O)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:11]2([CH2:13][CH2:12]2)[CH2:10][C@H:9]1[CH2:16][OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 2723981Borane;tetrahydrofuranHCID 66848235(S)-6-(tert-Butoxycarbonyl)-6-azaspiro[2.5]octane-5-carboxylic acid2회

생성물 1

HCID 66848101(S)-tert-butyl 5-(hydroxymethyl)-6-azaspiro[2.5]octane-6-carboxylate수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (S)-6-aza-spiro[2.5]octane-5,6-dicarboxylic acid 6-tert-butyl ester (intermediate 17, 35 g, 0.122 mol) in anhydrous THF (300 ml) was added BH3/THF (1M, 360 ml, 0.365 mol) under nitrogen at 0° C. After the addition was completed, the reaction mixture was warmed to room temperature and stirred at room temperature for overnight. The resulting mixture was evaporated to obtain a crude that was purified by silica gel chromatography (petroleum ether/ethyl acetate from 10/1 to 5/1). (S)-5-Hydroxymethyl-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester was obtained as colourless oil (31 g), yield:86%.

후처리

  1. additionAfter the addition
  2. customThe resulting mixture was evaporated
  3. customto obtain a crude that
  4. customwas purified by silica gel chromatography (petroleum ether/ethyl acetate from 10/1 to 5/1)

출처 및 근거

ORD 기록
ord-8700051f71a94f40b0aa90045d095a8d
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859608B2

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