Benzyl Alcohol → (4-(Tert-butyl-dimethyl-silanyloxy)-1-methyl-cyclohexyl)-carbamic acid benzyl ester

HRID 1293382Notes

Reaction equation

[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][CH:7]1[CH2:12][CH2:11][C:10]([CH3:16])(C(O)=O)[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].C([N:21]([CH2:24]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.[CH2:43]([OH:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C1(C)C=CC=CC=1>[CH2:43]([O:50][C:24](=[O:33])[NH:21][C:10]1([CH3:16])[CH2:9][CH2:8][CH:7]([O:6][Si:5]([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:17])[CH3:18])[CH2:12][CH2:11]1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of example 45C (832 mg, 3.05 mmol) and triethylamine (596 μL, 4.27 mmol) in toluene (15 mL) was added diphenylphosphoryl azide (791 μL, 3.66 mmol) via syringe. The resulting light amber solution was stirred at 23° C. for 1 hour, then benzyl alcohol (1.6 mL, 15.25 mmol) was added. The solution was then heated at 75° C. for 24 hours. The reaction mixture was cooled and the solvents removed in vacuo. The crude oil was purified by flash chromatography using a linear gradient of 95% hexane/5% ethyl acetate to 30% ethyl acetate/70% hexane to give the title compound (995 mg) as an inseparable mixture of diastereomers. MS (CI) m/z 378 (M+1)+; 1H NMR (300 MHz, DMSO) δ ppm 7.37-7.28 (m, 10H), 6.86 (s, 1H), 6.82 (s, 1H), 4.96 (s, 2H), 4.95 (s, 2H), 3.80-3.70 (m, 2H), 3.62-3.50 (m, 2H), 2.05 (d, 2H), 1.79-1.75 (m, 2H), 1.64-1.20 (m, 8H), 1.19 (s, 3H), 1.16 (s, 3H), 0.84 (s, 9H), 0.83 (s, 9H), 0.02 (s, 12 H).

Workup

temperatureThe solution was then heated at 75° C. for 24 hours
temperatureThe reaction mixture was cooled
customthe solvents removed in vacuo
customThe crude oil was purified by flash chromatography

Sources & evidence

ORD record: ord-b593c0c5a5454335bff2ec1dc862ec56
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238724B2

Reaction notes

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