3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)- → HCID 68809475, 화합물

HRID 434303

반응식

HRID 434303 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[C:16]([O:20][C:21]([N:23]1[C@@H:27]([CH:28]=O)[CH2:26][O:25][C:24]1([CH3:31])[CH3:30])=[O:22])([CH3:19])([CH3:18])[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.ClCCl>[C:16]([O:20][C:21]([N:23]1[C@@H:27]([CH2:28][N:13]2[CH2:14][CH2:15][CH:10]([C:8](=[O:9])[C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:11][CH2:12]2)[CH2:26][O:25][C:24]1([CH3:30])[CH3:31])=[O:22])([CH3:19])([CH3:17])[CH3:18]

참가 물질

6

반응물 3

HCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-HCID 27244404-(4-Fluorobenzoyl)piperidineHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 68809475HCID 68809475, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (4-fluoro-phenyl)-piperidin-4-yl-methanone (3.5 g, 17 mmol) in dry tetrahydrofuran (50 ml) is added (R)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (3.9 g, 17 mmol) and sodium triacetoxyborohydride (5.4 g, 25 mmol), and the reaction mixture stirred for 18 hours at ambient temperature. The reaction mixture is filtered and the solvent evaporated to give a white solid. The solid is taken up in dichloromethane (50 ml) and washed with saturated sodium bicarbonate solution (50 ml), water (2×50 ml) and brine (50 ml). The organic phase is dried over magnesium sulphate and evaporated to afford the product, [MH]+420.9.

후처리

  1. filtrationThe reaction mixture is filtered
  2. customthe solvent evaporated
  3. customto give a white solid
  4. washwashed with saturated sodium bicarbonate solution (50 ml), water (2×50 ml) and brine (50 ml)
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. customevaporated
  7. customto afford the product, [MH]+420.9

출처 및 근거

ORD 기록
ord-bcb2009a4e644e87a58309e501982678
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670379B2

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