Acetaldehyde → 5-Diethylaminomethyl-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966536노트

반응식

HRID 966536 반응식
Cl.[CH2:2]([O:9][C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][NH2:22])[CH:19]=2)[NH:14][C:13]=1[CH3:23])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:24](=O)[CH3:25].[C:27](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:28].[Na+]>ClC(Cl)C>[CH2:2]([O:9][C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][N:22]([CH2:24][CH3:25])[CH2:27][CH3:28])[CH:19]=2)[NH:14][C:13]=1[CH3:23])=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 1317251805-Aminomethyl-2-methyl-1h-indole-3-carboxylic acid benzyl ester, hydrochloride

생성물 1

HCID 99682915-Diethylaminomethyl-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester수율 34%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a mixture of 5-aminomethyl-2-methyl-1H-indole-3-carboxylic acid benzyl ester, hydrochloride (300 mg, 0.91 mmol, Example 63, Step E) and in dichloroethane (40 mL) was added acetaldehyde (0.1 mL, 1.82 mmol). The mixture was stirred for 0.5 hour and then sodium triacetoxyborohydride (289 mg, 1.37 mmol) was added. The mixture was stirred at room temperature overnight and then partitioned between methylene chloride and water. The organic phase was washed with saturated sodium bicarbonate solution and brine, dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo to give a solid residue, which was purified by chromatography (5%-15% methanol in methylene chloride) to give 107 mg (34%) of the desired product as a white solid: mp 106-108° C.; MS(APCI+): m/z 351.1 (MH+); Anal. Calcd for C22H26N2O2.0.25H2O: C, 74.44; H, 7.52; N, 7.89. Found: C, 74.30; H, 7.51; N, 7.79.

후처리

  1. stirringThe mixture was stirred at room temperature overnight
  2. custompartitioned between methylene chloride and water
  3. washThe organic phase was washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto give a solid residue, which
  8. customwas purified by chromatography (5%-15% methanol in methylene chloride)

출처 및 근거

ORD 기록
ord-a300d01a1c3345df9889101bae67ff50
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951848B2

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