Acetonitrile → (3S,4S)-3-Hydroxy-4-t-butyloxycarbonylamino-5-cyclohexylpentane nitrile

HRID 1722668Notes

Reaction equation

HRID 1722668 reaction equation
C([N-]C(C)C)(C)C.[Li+].[C:9](#[N:11])[CH3:10].[C:12]([O:16][C:17]([NH:19][C@@H:20]([CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[CH:21]=[O:22])=[O:18])([CH3:15])([CH3:14])[CH3:13]>O1CCCC1>[OH:22][C@H:21]([C@@H:20]([NH:19][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[CH2:10][C:9]#[N:11]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 2724682Lithium diisopropylamideHCID 10848617(S)-Tert-butyl 1-cyclohexyl-3-oxopropan-2-ylcarbamate

Product 1

HCID 10968477(3S,4S)-3-Hydroxy-4-t-butyloxycarbonylamino-5-cyclohexylpentane nitrileYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of lithium diisopropylamide (4.40 mmol) in dry tetrahydrofuran (4 mL) at -78° C. was added acetonitrile (0.25 mL, 4.4 mmol). To this enolate suspension was added 2(S)-t-butyloxycarbonylamino-3-cyclohexylpropanal (0.76 g, 2.98 mmol) in tetrahydrofuran (5 mL) pre-cooled to -78° C. After stirring for 15 minutes, the mixture was quenched with 2M HCl (5.0 mL), and extracted with ether which was dried over MgSO4 and evaporated. Flash chromatography on silica gel with ethyl acetate/hexane mixtures afforded 0.360 g (41%) of the desired compound as an oil.

Workup

  1. customthe mixture was quenched with 2M HCl (5.0 mL)
  2. extractionextracted with ether which
  3. dry with materialwas dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-cda5bcb397974507bfcfdb8e1c20aa41
Source dataset
uspto-grants-1989_08
Patent number
US04857507

Reaction notes

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