Lithium Hexamethyldisilazide → HCID 57794742, compound

HRID 2099267Notes

Reaction equation

HRID 2099267 reaction equation
CC1C=CC(S(O[C@@H:12]([CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:13][CH:14]([C:21]#[N:22])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=O)=O)=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>CN(C=O)C.CCOC(C)=O>[C:15]1([C@:14]2([C:21]#[N:22])[CH2:13][C@H:12]2[CH2:23][O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 57794772HCID 57794772, compound

Product 1

HCID 57794742HCID 57794742, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-42 °C

Procedure

To (1R)-3-cyano-3-phenyl-1-{[(phenylmethyl)oxy]methyl}propyl 4-methylbenzenesulfonate (7.4 g, 17.0 mmol), accessed via the method of preparation 2, in 70 mL DMF at −42° C. was added 1M lithium bis(trimethylsilyl)amide in hexanes (25.5 mL, 25.5 mmol, 1.5 eq) dropwise and stirred with continued cooling at −42° C. for 1 h. The reaction mixture was diluted with EtOAc, washed successively with water (4×) and brine, dried over MgSO4, filtered and concentrated to give the title compound (4.25 g, 16.1 mmol, 95%) as a yellow oil which was shown to be a 94:6 mix of the title compound to the product of Preparation 3B. 1H NMR (300 MHz, CDCl3) δ 7.42-7.29 (m, 10H), 4.64 (m, 2H), 3.91-3.86 (m, 1H), 3.74-3.68 (m,1H), 2.00-1.90 (m, 1H), 1.68-1.56 (m, 2H).

Workup

  1. washwashed successively with water (4×) and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cb84bb7b64be4bbeaedd1262b6241d06
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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