Chloroiodomethane → (4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride

HRID 559329노트

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HRID 559329 반응식
[CH2:1]([Zn]CC)C.[Cl:6]CI.C(OC([N:16]1[CH2:21][CH2:20][C:19](=[CH2:22])[CH:18]([OH:23])[CH2:17]1)=O)(C)(C)C>ClCCCl>[ClH:6].[CH2:22]1[C:19]2([CH2:20][CH2:21][NH:16][CH2:17][C@H:18]2[OH:23])[CH2:1]1

참가 물질

5

반응물 3

HCID 11644ChloroiodomethaneHCID 10584700tert-Butyl 3-hydroxy-4-methylidenepiperidine-1-carboxylateHCID 178418750HCID 178418750, 화합물

생성물 1

HCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride수율 36,664.699%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매2회

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온도
0 °C

실험 절차

To a solution of diethylzinc (1.1 M solution in toluene, 37.5 ml, 0.04 mmol) in 1,2-dichloroethane (80 ml) at 0° C. was added chloroiodomethane (5.99 ml, 0.08 mmol) under Ar. This mixture was stirred for 15 minutes before a solution of 3-hydroxy-4-methylene-piperidine-1-carboxylic acid tert-butyl ester (J. Org. Chem. 2001, 66, 2487) (4.19 g, 19.6 mmol) in 1,2-dichloroethane (10 ml) was added, after which time the reaction was stirred for 0.5 h at 0° C. and then allowed to reach room temperature, stirring for a further 1 h. The reaction was then quenched by addition of saturated aq. ammonium chloride solution, separated, and the organic dried (Na2SO4) and concentrated. Purification by flash column chromatography (ethyl acetate/heptane 2:8-1:1) afforded the title product (2.4 g, 54%) as a crystalline solid MS: 228.2 (MH+).

후처리

  1. additionwas added
  2. customto reach room temperature
  3. stirringstirring for a further 1 h
  4. customThe reaction was then quenched by addition of saturated aq. ammonium chloride solution
  5. customseparated
  6. dry with materialthe organic dried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification by flash column chromatography (ethyl acetate/heptane 2:8-1:1)

출처 및 근거

ORD 기록
ord-2e7967a7a7c94bc5bac14bfffe51af8e
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063042B2

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