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

HRID 2202684
ノート
印刷プレビュー

反応式

HRID 2202684 の反応式
[CH3:1][C:2]1([CH:6]=O)[CH2:5][CH2:4][CH2:3]1.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[CH:16]([O:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:17][NH2:18].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[CH:16]([O:19][Si:20]([CH2:21][CH3:22])([CH2:25][CH3:26])[CH2:23][CH3:24])[CH2:17][NH:18][CH2:6][C:2]1([CH3:1])[CH2:3][CH2:4][CH2:5]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 201345271-Methylcyclobutane-1-carbaldehydeHCID 1238562512-(2,6-Dichlorophenyl)-2-((triethylsilyl)oxy)ethanamine

生成物 1

HCID 1239798292-(2,6-dichlorophenyl)-N-((1-methylcyclobutyl)methyl)-2-((triethylsilyl)oxy)ethanamine収率 56.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

To a mixture of 1-methylcyclobutanecarbaldehyde (38.3 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 and then purified by prep TLC eluted with 5% MeOH/DCM to provide 2-(2,6-dichlorophenyl)-N-((1-methylcyclobutyl)methyl)-2-((triethylsilyl)oxy)ethanamine (89 mg, 0.221 mmol, 56.7% yield). 1H NMR (500 MHz, CDCl3) δ 7.18-7.22 (m, 2H), 6.98-7.10 (m, 1H), 5.57 (br. s., 1H), 3.30 (t, J=10.70 Hz, 1H), 2.74 (br. s., 1H), 2.60 (br. s., 1H), 2.51 (d, J=10.03 Hz, 1H), 1.68-1.89 (m, 4H), 1.60 (br. s., 2H), 1.47 (br. s., 1H), 1.03-1.14 (m, 3H), 0.76-0.84 (m, 9H), 0.41-0.54 (m, 6H); LCMS (ESI) m/z 402.4 (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. custompurified by prep TLC
  6. washeluted with 5% MeOH/DCM

出典と根拠

ORDレコード
ord-827326e76c1c4b498551ab6fb954ed28
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09365522B2

反応ノート

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