Acetic Acid → HCID 11719408, compound

HRID 353383Notes

Reaction equation

HRID 353383 reaction equation
[ClH:1].[OH:2][NH:3][C:4]([C:6]1([S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:11][CH2:10][N:9]([CH2:12][C:13]#[CH:14])[CH2:8][CH2:7]1)=[O:5].C(O)(=O)C.C(OC1(O[Si](C)(C)C)CC1)C.C([BH3-])#N.[Na+]>CO>[ClH:1].[CH:12]1([N:9]2[CH2:8][CH2:7][C:6]([S:15]([C:18]3[CH:19]=[CH:20][C:21]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:22][CH:23]=3)(=[O:17])=[O:16])([C:4]([NH:3][OH:2])=[O:5])[CH2:11][CH2:10]2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 11561491HCID 11561491, compound

Product 1

HCID 11719408HCID 11719408, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Part A: To a solution of the amine hydrochloride salt of Example 6, part E (2.13 g, 5.0 mmol) in methanol (25 mL) was added 3A molecular sieves, acetic acid (2.86 mL, 50 mmol) and the solution was stirred for 5 minutes. To this solution was added ((1-ethyoxycyclopropyl)oxy)-trimethylsilane (6.08 mL, 30 mmol) followed by sodium cyanoborohydride (1.41 g, 22.0 mmol), and the solution was heated to reflux for 18 hours. The excess salts and sieves were collected by filtration and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate and washed with 1N NaOH, H2O and saturated NaCl, and dried over magnesium sulfate. Chromatography (on silica, ethyl acetate/hexane) provided the cyclopropyl amine as a white solid (1.90 g, 86%).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 18 hours
  3. filtrationThe excess salts and sieves were collected by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with 1N NaOH, H2O and saturated NaCl
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-9d0749e9e6a2424fb7db15fdd1758153
Source dataset
uspto-grants-2004_06
Patent number
US06750233B2

Reaction notes

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