Triethylamine → HCID 67109854, compound

HRID 1259489Notes

Reaction equation

HRID 1259489 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[O:15][CH2:14][CH2:13][NH:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:23][CH2:24][CH2:25][CH2:26]I>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH:10]1[O:15][CH2:14][CH2:13][N:12]([CH2:26][CH2:25][CH2:24][Cl:23])[CH2:11]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 813631-Chloro-3-iodopropaneHCID 67110015HCID 67110015, compound

Product 1

HCID 67109854HCID 67109854, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholine (2.1 g, 9.07 mmol) in DCM (20 mL) was treated with triethylamine (3.8 mL, 27.2 mmol) and 1-chloro-3-iodopropane (1.95 mL, 18.1 mmol). The reaction mixture was stirred at rt overnight. The reaction mixture was concentrated under reduced pressure then purified by MPLC (ISCO, 0% MeOH/100% DCM to 25% MeOH/75% DCM). The product was isolated as an oil (560 mg, 20%): HPLC MS RT=2.66 min, MH+=308.4, 310.4; 1H NMR (DMSO-d6) δ: 3.79-3.69 (1H, m), 3.63 (2H, t) 3.59-3.52 (1H, m), 3.50-3.36 (3H, m), 2.73 (1H, d), 2.61 (1H, d), 2.35 (2H, t), 1.94 (1H, td), 1.83 (2H, qt), 1.73 (1H, t), 0.83 (9H, s), 0.00 (6H, s).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthen purified by MPLC (ISCO, 0% MeOH/100% DCM to 25% MeOH/75% DCM)

Sources & evidence

ORD record
ord-18e638d5e27b4e99ac8bae6b35201c4c
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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