Dichloromethane → N-Boc-undecane-1,11-diamine

HRID 2188800노트

반응식

HRID 2188800 반응식
C(O[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(OC(C)(C)C)=[O:2].[CH2:16]([NH2:28])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH2:27].C(N(C(C)C)CC)(C)C.ClCCl>CO>[OH-:2].[NH4+:27].[NH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:28][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 699661,11-UndecanediamineHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonate

생성물 2

HCID 14923Ammonium Hydroxide수율 10%HCID 16221264N-Boc-undecane-1,11-diamine수율 95%

시약·촉매·용매 1

HCID 887Methanol용매3회

실험 절차

Using a syringe pump, a solution of di-tert-butyl dicarbonate (2.50 g, 11.45 mmol) in methanol (50 mL) was added to a stirred solution of undecane 1,11-diamine (6) (3.00 g, 16.10 mmol) and diisopropylethylamine (2.90 mL, 16.60 mmol) in methanol (200 mL) over 10 h, and the resulting reaction mixture was stirred at rt for 12 h. The reaction was then concentrated to a white solid. Purification by column chromatography (silica gel, 10:90 methanol/dichloromethane, then 20:80 (10% concentrated ammonium hydroxide in methanol)/dichloromethane) afforded the protected amine 7 (2.19 g, 67% yield) as a white solid: 1H NMR (300 MHz, CD3OD) δ 1.30 (br s, 14H), 1.43 (br s, 13H), 2.61 (t, 2H), 3.00 (t, 2H).

후처리

  1. customthe resulting reaction mixture
  2. concentrationThe reaction was then concentrated to a white solid
  3. customPurification by column chromatography (silica gel, 10:90 methanol/dichloromethane

출처 및 근거

ORD 기록
ord-5c3d66807eec46d78f893e7b486f91e7
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324218B2

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