Triethylamine → (S)-4-((tert-butyldiphenylsilyloxy)methyl)-1-(1-adamantylmethyl)imidazolidin-2-one

HRID 75160Notes

Reaction equation

HRID 75160 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[Si:13]([O:30][CH2:31][C@@H:32]([NH2:46])[CH2:33][NH:34][CH2:35][C:36]12[CH2:45][CH:40]3[CH2:41][CH:42]([CH2:44][CH:38]([CH2:39]3)[CH2:37]1)[CH2:43]2)([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl.O>[Si:13]([O:30][CH2:31][C@@H:32]1[CH2:33][N:34]([CH2:35][C:36]23[CH2:37][CH:38]4[CH2:39][CH:40]([CH2:41][CH:42]([CH2:44]4)[CH2:43]2)[CH2:45]3)[C:5](=[O:11])[NH:46]1)([C:26]([CH3:27])([CH3:28])[CH3:29])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 68474186(S)-3-(tert-butyldiphenylsilyloxy)-N1-(1-adamantylmethyl)propane-1,2-diamine

Product 1

HCID 68477189(S)-4-((tert-butyldiphenylsilyloxy)methyl)-1-(1-adamantylmethyl)imidazolidin-2-oneYield 156.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of triphosgene (124 mg, 0.42 mmol) in anhydrous CH2Cl2 (2 mL) was added slowly to a solution of (S)-3-(tert-butyldiphenylsilyloxy)-N1-(1-adamantylmethyl)propane-1,2-diamine (600 mg, 1.26 mmol) and triethylamine (140 mg, 1.4 mmol) in anhydrous CH2Cl2 (10 mL) at 0° C. The reaction mixture was stirred for another 1 h. The mixture was diluted with water and extracted with CH2Cl2 (50 mL). The organic layer was washed with 0.1 N aq HCl (2×20 mL) and brine (10 mL), dried over MgSO4 and concentrated to give a residue, which was purified by preparative TLC to provide (S)-4-((tert-butyldiphenylsilyloxy)methyl)-1-(1-adamantylmethyl)imidazolidin-2-one (330 mg, 52%). 1H NMR: (CDCl3, 400 MHz): δ=1.05 (s, 9H), 1.54 (s, 6H), 1.62-1.73 (m, 8H), 1.98 (s, 3H), 2.77 (m, 2H), 3.21 (m, 1H), 3.55 (t, 1H), 3.65 (m, 2H), 3.82 (m, 1H), 4.57 (s, 1H), 7.4 (m, 6H), 7.62 (m, 4H).

Workup

  1. extractionextracted with CH2Cl2 (50 mL)
  2. washThe organic layer was washed with 0.1 N aq HCl (2×20 mL) and brine (10 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give a residue, which
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-a76ab5b3ff1a46f1917033eeac87f620
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Reaction notes

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