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

HRID 2188800ノート

反応式

HRID 2188800 の反応式
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]

参加物

7

反応物 4

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

生成物 2

HCID 14923Ammonium Hydroxide収率 10%HCID 16221264N-Boc-undecane-1,11-diamine収率 95%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒3 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5c3d66807eec46d78f893e7b486f91e7
出典データセット
uspto-grants-2012_12
特許番号
US08324218B2

反応ノート

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