HCID 86653081, compound → HCID 67191992, compound

HRID 2355434Notes

Reaction equation

HRID 2355434 reaction equation
[CH3:1][Si:2]([CH3:23])([CH3:22])[CH2:3][CH2:4][O:5][C:6](=[O:21])[N:7]([CH2:9][C@@H:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:11]=[O:12])[CH3:8].[CH:24]1([Mg]Cl)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C1(C)C=CC=CC=1>[C:17]([O:16][C:14]([NH:13][C@H:10]([CH2:9][N:7]([CH3:8])[C:6]([O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:22])[CH3:23])=[O:21])[C@@H:11]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[OH:12])=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 86653081HCID 86653081, compoundHCID 178478990HCID 178478990, compound

Product 1

HCID 67191992HCID 67191992, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of above crude (2-(trimethylsilyl)ethyl)(R)-2-(t-butoxycarbonylamino)-2-formylethylmethylcarbamate (0.71 g, 2.05 mmol) in toluene (6 mL) at −78° C. was added cyclohexylmagnesium chloride (2 M in ether, 5.13 mL) dropwise. The resulting solution was stirred at −78° C. for 1 h, allowed to warm slowly to rt, and quenched with sat'd aq NH4Cl (5 mL). The organic layer was separated, and aqueous layer was extracted with ether (2×5 mL). The combined organic layers were concentrated in vacuo, and the residue was purified by flash column chromatography to give (1R,2R)-2-(t-butoxycarbonylamino)-1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-1-ol (209.7 mg, 24%). 1H NMR (400 MHz, CDCl3): 4.94 (d, 1H), 4.16 (m, 2H), 3.80 (m, 1H), 3.78 (m, 1H), 3.04 (m, 1H), 2.88 (m, 1H), 2.86 (s, 3H), 2.10 (m, 1H), 1.64 (m, 4H), 1.42 (m, 1H), 1.40 (s, 9H), 1.28-1.02 (m, 4H), 0.98 (m, 2H), 0.82 (m, 4H), 0.02 (s, 9H); MS m/z 431 (M+H+).

Workup

  1. temperatureto warm slowly to rt
  2. customquenched with sat'd aq NH4Cl (5 mL)
  3. customThe organic layer was separated
  4. extractionaqueous layer was extracted with ether (2×5 mL)
  5. concentrationThe combined organic layers were concentrated in vacuo
  6. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-241ce5d534624ee383b86c7a832573a8
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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