Water → HCID 21971165, compound

HRID 750398Notes

Reaction equation

HRID 750398 reaction equation
[CH:1]([C@@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:5][CH2:6][CH3:7])=[O:2].O.CC(C)(O)[C:19]#[N:20].[C-]#N.[K+]>C1(C)C=CC=CC=1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:19]([CH:1]([OH:2])[C@@H:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:5][CH2:6][CH3:7])#[N:20]

Participants

7

Reactant 4

HCID 962WaterHCID 6406Acetone CyanohydrinHCID 9032Potassium CyanideHCID 10420833(S)-tert-butyl 1-oxohexan-2-ylcarbamate

Product 1

HCID 21971165HCID 21971165, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of tert-butyl (1S)-1-formylpentylcarbamate in toluene was added water (50 mL), acetone cyanohydrin (16.4 mL, 180.0 mmol), potassium cyanide (250 mg) and tetrabutylammonium iodide (300 mg). The mixture was stirred at ambient temperature for 20 h, and then the layers were separated. The organic layer was washed with water (5×60 mL), dried with magnesium sulfate and concentrated in vacuo to afford the title compound (26.7 g, 92%) as a thick oil. The 1H NMR spectrum showed an approximately equal mixture of diastereomers. 1H NMR (400 MHz, DMSO-d6): δ 6.91,6.83 (2d, J=8 Hz, J=9 Hz, 1H), 6.54, 6.47 (2d, J=7 Hz, J=6 Hz, 1H), 4.44, 4.17 (2t, J=5 Hz, J=8 Hz, 1H), 3.60-3.50 (m, 1H), 1.65-1.10 (m, 6H), 1.34 (s, 9H), 0.80 (t, J=6 Hz, 3H).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water (5×60 mL)
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d51c1b1b02f42b38147c0462639f914
Source dataset
uspto-grants-2008_07
Patent number
US07402606B2

Reaction notes

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