Benzylamine → HCID 178455053、化合物

HRID 585654

反応式

HRID 585654 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 equipped with magnetic stirrer was loaded 4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanone (3.20 g, 7.36 mmol). Anhydrous 1,2-dichloroethane (85 ml) was added, and to the stirred solution was added benzylamine (0.97 ml, 8.83 mmol) as a solution in 1,2-dichloroethane (20 ml). Activated powdered 4 Å molecular sieves (5.80 g) were added and the reaction mixture stirred vigorously for 2.5 hr. Tetramethylammoniumtriacetoxyborohydride (2.90 g, 11.0 mmol) 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 then 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 product (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. customTo a round bottomed flask equipped with magnetic stirrer
  2. additionwere added
  3. stirringthe reaction mixture stirred for 64 hr at room temperature
  4. stirringvigorous stirring
  5. waitwas continued for 0.5 hr
  6. filtrationThe reaction mixture was then filtered through celite
  7. washwashing with dichloromethane (100 ml)
  8. customThe layers were separated
  9. extractionthe aqueous layer was extracted with dichloromethane (2×50 ml)
  10. washThe combined organic phases were washed with brine (100 ml)
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customaffording the crude product
  15. customPurification via flash column chromatography (
  16. washSiO2, ethyl acetate/petroleum ether, gradient elution

出典と根拠

ORDレコード
ord-805600af6cb44f7fa46dc31589387189
出典データセット
uspto-grants-2005_08
特許番号
US06933319B2

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