N,N,N',N'-Tetramethylethylenediamine → 3-Boc-4(S)-Cyclohexylmethyl-2,2-dimethyl-5(R,S)-[2-(4(S,S)-sec.-butyloxazolin-2-yl)ethyl]oxazolidine

HRID 1722266Notes

Reaction equation

HRID 1722266 reaction equation
[C@@H:1]([C@H:5]1[CH2:9][O:8][C:7]([CH3:10])=[N:6]1)([CH2:3][CH3:4])[CH3:2].CN(C)CCN(C)C.C([Li])CCC.[C:24]([N:31]1[C@@H:35]([CH2:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[CH:34]([CH2:43]I)[O:33][C:32]1([CH3:46])[CH3:45])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C([O-])(O)=O.[Na+]>C1COCC1.CCCCCC>[C:24]([N:31]1[C@@H:35]([CH2:36][CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[CH:34]([CH2:43][CH2:10][C:7]2[O:8][CH2:9][C@H:5]([C@H:1]([CH2:3][CH3:4])[CH3:2])[N:6]=2)[O:33][C:32]1([CH3:45])[CH3:46])([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25]

Participants

8

Reactant 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 516892Sodium BicarbonateHCID 186342744(S,S)-sec.-butyl-2-methyloxazolineHCID 1317160313-Boc-4(S)-cyclohexylmethyl-2,2-dimethyl-5(R,S)-iodomethyloxazolidineHCID 178418339Butyllithium

Product 1

HCID 1317160303-Boc-4(S)-Cyclohexylmethyl-2,2-dimethyl-5(R,S)-[2-(4(S,S)-sec.-butyloxazolin-2-yl)ethyl]oxazolidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

3.76 g of 4(S,S)-sec.-butyl-2-methyloxazoline and 4.0 ml of N,N,N',N'-tetramethylethylenediamine are dissolved in 100 ml of THF and, at -78° C., added dropwise to 14.9 ml of a 1.6M solution of n-butyllithium in hexane are added dropwise. The mixture is stirred at this temperature for 30 min and then 1.15 g of 3-Boc-4(S)-cyclohexylmethyl-2,2-dimethyl-5(R,S)-iodomethyloxazolidine in 10 ml of THF are added dropwise. The reaction solution is stirred at R.T. for 1 h and is poured into 200 ml of saturated aqueous NaHCO3 solution, and the mixture is extracted 3 times with 200 ml of EA. Drying over Na2SO4 and concentration in vacuo is followed by chromatography on silica gel (mobile phase MTB/diisopropyl ether 1:1). The title compound is obtained as a colorless oil.

Workup

  1. additionare added dropwise
  2. stirringThe reaction solution is stirred at R.T. for 1 h
  3. extractionthe mixture is extracted 3 times with 200 ml of EA
  4. dry with materialDrying over Na2SO4 and concentration in vacuo

Sources & evidence

ORD record
ord-bb2272c52548452ca097837ee30d36fa
Source dataset
uspto-grants-1989_08
Patent number
US04855286

Reaction notes

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