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

HRID 2188800Notes

Reaction equation

HRID 2188800 reaction equation
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]

Participants

7

Reactant 4

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

Product 2

HCID 14923Ammonium HydroxideYield 10%HCID 16221264N-Boc-undecane-1,11-diamineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5c3d66807eec46d78f893e7b486f91e7
Source dataset
uspto-grants-2012_12
Patent number
US08324218B2

Reaction notes

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