Hexane → HCID 13891111, compound

HRID 982020Notes

Reaction equation

HRID 982020 reaction equation
C([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH:10]([OH:13])[CH:11]=[CH2:12])=O)(C)(C)C.[H-].[Na+].CCCCCC>CN(C)C=O>[CH:15]1([CH2:14][C@H:9]2[CH:10]([CH:11]=[CH2:12])[O:13][C:6](=[O:5])[NH:8]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8058HexaneHCID 24758Sodium hydrideHCID 138911064(S)-t-Butyloxycarbonylamino-5-cyclohexyl-3(R,S)hydroxy-1-pentene

Product 1

HCID 13891111HCID 13891111, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The resultant product of Example 1 (2.80 g, 9.88 mmol) in dry dimethylformamide (DMF) (50 ml) was added to a stirred suspension of NaH (593 mg of a 60% dispersion in oil, 14.8 mmol, hexane washed) in dry DMF (50 ml). After 3 h, the mixture was quenched (750 ml water+100 ml brine) and extracted with ether (5×100 ml). The combined organic phase was washed with brine (3×50 ml), dried (MgSO4), filtered and evaporated to an oil (2.23 g). The NMR spectrum of the crude product revealed an 82:18 mixture of 5S:5R diastereomers. Silica gel chromatography gave 80% recovery of pure diastereomers. 5S:

Workup

  1. washwashed) in dry DMF (50 ml)
  2. customthe mixture was quenched (750 ml water+100 ml brine)
  3. extractionextracted with ether (5×100 ml)
  4. washThe combined organic phase was washed with brine (3×50 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to an oil (2.23 g)
  8. additionan 82:18 mixture of 5S
  9. customSilica gel chromatography gave 80% recovery of pure diastereomers

Sources & evidence

ORD record
ord-10e892cd15504d22bd314b438f6799b1
Source dataset
uspto-grants-1991_02
Patent number
US04994477

Reaction notes

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