Benzylamine → HCID 178455053、化合物

HRID 1007953

反応式

HRID 1007953 の反応式
[Si:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:12]=[CH:11][C:10]=1[CH:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.[OH-].[Na+]>ClCCCl>[CH2:30]([NH:37][C@H:26]1[CH2:27][CH2:28][C@@H:23]([C:10]2[CH:11]=[CH:12][C:13]([O:15][Si:16]([C:19]([CH3:21])([CH3:22])[CH3:20])([CH3:17])[CH3:18])=[CH:14][C:9]=2[O:8][Si:1]([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3])[CH2:24][CH2:25]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

参加物

6

反応物 4

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 223378144-(2,4-Bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexan-1-one

生成物 1

HCID 178455053HCID 178455053、化合物収率 70%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

実験手順

To a round bottomed flask was charged 4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl) cyclohexanone (3.20 g), 1,2-dichloroethane (85 ml), and to the stirred solution was added benzylamine (0.97 ml) as a solution in 1,2-dichloroethane (20 ml) followed by activated powdered 4 Å molecular sieves (5.80 g) and the reaction mixture stirred for 2.5 hr. Tetramethylammoniumtriacetoxyborohydride (2.90 g) was added in one portion and the reaction mixture stirred for 64 hr at room temperature. Aqueous sodium hydroxide solution (30 ml, 0.4M) was added and vigorous stirring was continued for 0.5 hr. The reaction mixture was filtered through celite, washing with dichloromethane (100 ml). The layers were separated and the aqueous layer was extracted with dichloromethane (2×50 ml). The combined organic phases were washed with brine (100 ml), dried over magnesium sulfate, filtered and concentrated in vacuo affording the-crude product. Purification via flash column chromatography (SiO2, ethyl acetate/petroleum ether, gradient elution using 1:9, 1:4, then 3:7 v/v) furnished the title compound (2.69 g, 70%) as a pale yellow oil. δH(CDCl3) 0.01 (6H, s), 0.05 (6H, s), 0.77 (9H, s), 0.83 (9H, s), 1.31 (1H, br), 1.39 (4H, m), 1.52 (2H, m), 1.70 (2H, m), 2.69 (1H, m), 2.75 (1H, m), 6.10 (1H, d), 6.23 (1H, dd), 6.84 (1H, d), 7.15 (5H, m).

後処理

  1. stirringthe reaction mixture stirred for 64 hr at room temperature
  2. stirringvigorous stirring
  3. waitwas continued for 0.5 hr
  4. filtrationThe reaction mixture was filtered through celite
  5. washwashing with dichloromethane (100 ml)
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with dichloromethane (2×50 ml)
  8. washThe combined organic phases were washed with brine (100 ml)
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customaffording the-crude product
  13. customPurification via flash column chromatography (
  14. washSiO2, ethyl acetate/petroleum ether, gradient elution

出典と根拠

ORDレコード
ord-46df1cb2a01f4b158791f636e274653f
出典データセット
uspto-grants-2004_09
特許番号
US06797731B2

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