HCID 85225451, compound → HCID 85266867, compound

HRID 399317Notes

Reaction equation

HRID 399317 reaction equation
[CH3:1][Mg]Br.[CH:4]1([CH:10]2[CH:14]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[O:13][B:12]([CH:21](Cl)[CH2:22][CH:23]([CH3:28])[C:24]([CH2:26][CH3:27])=[CH2:25])[O:11]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1>C1COCC1>[CH:4]1([CH:10]2[CH:14]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[O:13][B:12]([CH:21]([CH3:1])[CH2:22][CH:23]([CH3:28])[C:24]([CH2:26][CH3:27])=[CH2:25])[O:11]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 85225451HCID 85225451, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 85266867HCID 85266867, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (3.0 M in ether, 13.3 mL, 40 mmol) was added to a stirred solution of [4R-[2(S*,S*),4α,5β]]-4,5-dicyclohexyl-2-(5-chloro-2-ethyl-3-methylpenten-5-yl)-1,3,2-dioxaborolane (15.2 g, 40 mmol) in THF (250 mL) at -78° C. over a period of 20 min. The bath was allowed to warm to 20°-25° C. and the reaction mixture was stirred for 20 h. The solution was concentrated under vacuum and ether (200 mL) was added to the residue. The ethereal solution was washed with saturated aqueous ammonium chloride (2∞200 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to liquid [4R-[2(S*,S*),4α,5β]]-4,5-dicyclohexyl-2-(2-ethyl -3,5-dimethylpenten-5-yl)-1,3,2-dioxaborolane (12a) (13.8 g, 96%); 300 MHz 1H-NMR (CDCl3) δ0.84-2.27 (m, 37), 3.81 (m, 2), 4.68 and 4.74 (AB, 2); 75 MHz 13C-NMR (CDCl3) 12.3, 16.2, 20.2, 25.9, 26.0, 26.4, 27.4, 28.28, 28.34, 39.2, 39.5, 43.0, 83.2, 106.7, 156.3). HRMS: calcd for C23H41BO2 (M+) 360.3200, found: 360.3199.

Workup

  1. temperatureto warm to 20°-25° C.
  2. concentrationThe solution was concentrated under vacuum and ether (200 mL)
  3. additionwas added to the residue
  4. washThe ethereal solution was washed with saturated aqueous ammonium chloride (2∞200 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum to liquid [4R-[2(S*,S*),4α,5β]]-4,5-dicyclohexyl-2-(2-ethyl -3,5-dimethylpenten-5-yl)-1,3,2-dioxaborolane (12a) (13.8 g, 96%)

Sources & evidence

ORD record
ord-930226320390480e8cb7fc01ddfcfbf9
Source dataset
uspto-grants-1998_10
Patent number
US05817882

Reaction notes

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