2-Pyridinecarboxaldehyde → Tert-butyl 2-((8-(tert-butoxycarbonylamino)octyl)(pyridin-2-ylmethyl)amino)acetate

HRID 1509780ノート

反応式

HRID 1509780 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[C:40]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])(=[O:43])[CH:41]=O>ClCCCl.CC(O)=O>[C:13]([O:12][C:11]([NH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:1]([CH2:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=1)[CH2:41][C:40]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[O:17])([CH3:14])([CH3:16])[CH3:15]

参加物

7

反応物 4

HCID 142732-PyridinecarboxaldehydeHCID 4086223Tert-butyl (8-aminooctyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 10986247Tert-butyl 2-oxoacetate

生成物 1

HCID 59404338Tert-butyl 2-((8-(tert-butoxycarbonylamino)octyl)(pyridin-2-ylmethyl)amino)acetate収率 58%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 176Acetic Acid溶媒

反応条件

温度
0 °C

実験手順

A solution of tert-butyl 8-aminooctylcarbamate (1.61 g, 6.588 mmol), 2-pyridinecarboxaldehyde (0.63 mL, 6.588 mmol) and AcOH (0.10 mL) in DCE (30 mL) was heated at 75° C. for 30 min under nitrogen. The reaction mixture was cooled to 0° C., and treated sequentially with NaBH(OAc)3 (3.708 g, 17.5 mmol) and tert-butyl glyoxalate (1.53 g)1. The reaction mixture was stirred at room temperature overnight and quenched with water. The reaction mixture was then extracted with DCM and the organic layers was dried and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford tert-butyl 2-((8-(tert-butoxycarbonylamino)octyl)(pyridin-2-ylmethyl)amino)acetate (1.71 g, 58%) as a yellow oil. 1H NMR (400 MHz, CD3Cl3) δ 8.52 (d, J=4.8 Hz, 1H), 7.65 (td, J=7.8, 1.6 Hz, 1H), 7.56 (d, J=7.6, 1H), 7.18-7.12 (m, 1H), 4.50 (s, 1H), 3.90 (s, 2H), 3.28 (s, 2H), 3.07 (q, J=6.3 Hz, 2H), 2.61 (t, J=7.6 Hz, 2H), 1.50-1.24 (m, 30H); ESMS m/z: 450.4 (M+H)+.

後処理

  1. customquenched with water
  2. extractionThe reaction mixture was then extracted with DCM
  3. customthe organic layers was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography over silica gel

出典と根拠

ORDレコード
ord-2c7742aaa236405882ca39dc889355b0
出典データセット
uspto-grants-2012_07
特許番号
US08211402B2

反応ノート

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