Benzyl isocyanate → HCID 178522839, compound

HRID 1007975Notes

Reaction equation

HRID 1007975 reaction equation
C(N(CC)C(C)C)(C)C.[CH2:10]([N:17]=[C:18]=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Si]([O:27][C:28]1[CH:33]=[C:32]([O:34][Si](C(C)(C)C)(C)C)[CH:31]=[CH:30][C:29]=1[C@H:42]1[CH2:47][CH2:46][C@H:45]([OH:48])[CH2:44][CH2:43]1)(C(C)(C)C)(C)C>CN(C)C=O>[CH2:10]([NH:17][C:18](=[O:19])[O:48][C@H:45]1[CH2:44][CH2:43][C@H:42]([C:29]2[CH:30]=[CH:31][C:32]([OH:34])=[CH:33][C:28]=2[OH:27])[CH2:47][CH2:46]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 76639Benzyl isocyanateHCID 81531DiisopropylethylamineHCID 178455059HCID 178455059, compound

Product 1

HCID 178522839HCID 178522839, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (398 μl) and benzylisocyanate (154 μl) was added to a stirred solution of trans-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanol (200 mg) in anhydrous dimethylformamide (1 ml). After 16 hr at 50° C., the reaction mixture was partitioned between ethyl acetate (50 ml) and water (50 ml) and stirred for 16 hr at room temperature. The aqueous layer was extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with brine (50 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was purified using flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v) to give the title compound (20 mg, 13%) as a pale yellow gum. δH (CD3OD) 1.40-1.60 (4H, m), 1.80-1.90 (2H, m), 1.00-1.20 (2H, m), 2.70-2.82 (1H, m), 4.20-4.30 (2H, s), 4.55-4.65 (1H, m), 6.20-6.30 (2H, m), 6.86 (1H, d), 7.15-7.40 (5H, m); m/z (ES+) 342 (M+H+).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate (50 ml) and water (50 ml)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 ml)
  3. washThe combined organic extracts were washed with brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-8cea353eba5b4ac49e097974a95c063f
Source dataset
uspto-grants-2004_09
Patent number
US06797731B2

Reaction notes

Loading…