3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)- → HCID 68809475、化合物

HRID 434303ノート

反応式

HRID 434303 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 68809475HCID 68809475、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bcb2009a4e644e87a58309e501982678
出典データセット
uspto-grants-2003_12
特許番号
US06670379B2

反応ノート

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