Lithium Hexamethyldisilazide → HCID 57794765, compound

HRID 2099268Notes

Reaction equation

HRID 2099268 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CC1C=CC(S(O[C@@H:22]([CH2:33][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:23][CH:24]([C:31]#[N:32])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:25]1([C@@:24]2([C:31]#[N:32])[CH2:23][C@H:22]2[CH2:33][O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 57794772HCID 57794772, compound

Product 1

HCID 57794765HCID 57794765, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 765 mL toluene cooled to 0° C. was added 1.0 M LHMDS in hexanes (148.1 mL, 148.1 mmol, 1 eq). To this solution was added (1R)-3-cyano-3-phenyl-1-{[(phenylmethyl)oxy]methyl}propyl 4-methylbenzenesulfonate (43.0 g, 98.73 mmol, 1 eq), accessed via the method of Preparation 2, in 236 mL toluene. The reaction mixture was stirred at 0° C. for 16 h, then washed successively with water and brine, dried over MgSO4, filtered and concentrated to give a yellow oil that was shown to be an 8:2 diastereomeric mixture of the title compound to the product of Preparation 3A. The desired diastereomer (16.0 g, 62%) was separated by silica gel flash chromatography using 9:1→8:2 hexanes in ethyl acetate. 1H NMR (300 MHz, CDCl3) δ 7.44-7.15 (m, 10H), 4.28-4.19 (m, 2H), 3.31-3.27 (m, 1H), 2.94-2.84 (m, 1H), 2.22-2.15 (m,1H), 1.76-1.72 (m, 1H), 1.47-1.44 (m, 1H). ES-LCMS m/z 264.1 (M+H).

Workup

  1. washwashed successively with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a yellow oil that

Sources & evidence

ORD record
ord-312b79fde15e4b10acf58c92bc0b683c
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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