3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)- → HCID 68809159, 화합물

HRID 434299

반응식

HRID 434299 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH:13]=O)[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:25])=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][N:29]2[CH2:30][CH2:31][CH:26]([C:24](=[O:25])[C:21]3[CH:20]=[CH:19][C:18]([Cl:17])=[CH:23][CH:22]=3)[CH2:27][CH2:28]2)[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-HCID 27771154-(4-Chlorobenzoyl)PiperidineHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 68809159HCID 68809159, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (R)4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.5 g, 2.18 mmol) in tetrahydrofuran (15 ml) is added (4-chloro-phenyl)-piperidin-4-yl-methanone (0.49 g, 2.18 mmol) and sodium triacetoxyborohydride (0.69 g, 3.27 mmol), and the reaction mixture stirred for 3.5 hours at ambient temperature. The solvent is evaporated and the residue partitioned between ethyl acetate (50 ml) and saturated sodium bicarbonate solution (50 ml). The ethyl acetate is dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography (ethyl acetate:hexane, 1:1 elution) to afford (S)-4-[4-(4-chloro-benzoyl)-piperidin-1-ylmethyl]-2,2-dimethyl-oxazoldine-3-carboxylic acid tert-butyl ester, [MH]+437.2.

후처리

  1. customThe solvent is evaporated
  2. customthe residue partitioned between ethyl acetate (50 ml) and saturated sodium bicarbonate solution (50 ml)
  3. dry with materialThe ethyl acetate is dried over magnesium sulphate
  4. customevaporated
  5. customThe crude product is purified by flash silica chromatography (ethyl acetate:hexane, 1:1 elution)

출처 및 근거

ORD 기록
ord-289e5a0a2c844c5689bd9fe851d1b3ea
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670379B2

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