Sodium triacetoxyborohydride → 2-(2,6-dichlorophenyl)-N-((1-methylcyclopropyl)methyl)-2-((triethylsilyl)oxy)ethanamine

HRID 2202681ノート

反応式

HRID 2202681 の反応式
[CH3:1][C:2]1([CH:5]=O)[CH2:4][CH2:3]1.[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[CH:15]([O:18][Si:19]([CH2:24][CH3:25])([CH2:22][CH3:23])[CH2:20][CH3:21])[CH2:16][NH2:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[CH:15]([O:18][Si:19]([CH2:20][CH3:21])([CH2:24][CH3:25])[CH2:22][CH3:23])[CH2:16][NH:17][CH2:5][C:2]1([CH3:1])[CH2:3][CH2:4]1

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 101976191-Methylcyclopropane-1-carbaldehydeHCID 1238562512-(2,6-Dichlorophenyl)-2-((triethylsilyl)oxy)ethanamine

生成物 1

HCID 1231605382-(2,6-dichlorophenyl)-N-((1-methylcyclopropyl)methyl)-2-((triethylsilyl)oxy)ethanamine収率 62.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 1-methylcyclopropanecarbaldehyde (32.8 mg, 0.390 mmol) in DCM (2.0 ml) was added 2-(2,6-dichlorophenyl)-2-((triethylsilyl)oxy)ethanamine (125 mg, 0.390 mmol) followed by NaBH(OAc)3 (124 mg, 0.585 mmol). After 45 min, this was quenched with sat. aq. NaHCO3. The layers were separated. The aqueous layer was extracted with DCM. The combined organic layers were concentrated then purified by prep TLC eluted with 5% MeOH/DCM to provide 2-(2,6-dichlorophenyl)-N-((1-methylcyclopropyl)methyl)-2-((triethylsilyl)oxy)ethanamine (95 mg, 0.245 mmol, 62.7% yield). 1H NMR (500 MHz, CDCl3) δ 7.28-7.30 (m, 2H), 7.12-7.16 (m, 1H), 5.65 (br. s., 1H), 3.37-3.44 (m, 1H), 2.82-2.90 (m, 1H), 2.69 (br. s., 1H), 2.48 (d, J=11.86 Hz, 1H), 1.60 (br. s., 1H), 1.15 (s, 3H), 0.87-0.92 (m, 9H), 0.51-0.63 (m, 6H), 0.28-0.44 (m, 4H); LCMS (ESI) m/z 388.3 (M+H)+.

後処理

  1. customthis was quenched with sat. aq. NaHCO3
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with DCM
  4. concentrationThe combined organic layers were concentrated
  5. customthen purified by prep TLC
  6. washeluted with 5% MeOH/DCM

出典と根拠

ORDレコード
ord-6623c6276fb248f8b18fc8358450c79e
出典データセット
uspto-grants-2016_06
特許番号
US09365522B2

反応ノート

読み込み中…