Acetone Cyanohydrin → HCID 21971165, compound

HRID 1953434Notes

Reaction equation

HRID 1953434 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][OH:11])=[O:7])([CH3:4])[CH3:3].CC(C)(O)[C:18]#[N:19].C(N(CC)CC)C>>[OH:11][CH:10]([C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:12][CH2:13][CH2:14][CH3:15])[C:18]#[N:19]

Participants

4

Reactant 3

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 13969856(S)-tert-butyl 1-hydroxyhexan-2-ylcarbamate

Product 1

HCID 21971165HCID 21971165, compoundYield 79.9%

Procedure

40 g (200 mmol) of (S)-2-[N-(2-methyl-2-propyloxycarbonyl)amino]hexanol was dissolved in 300 ml of anhydrous methylenechroride, 34 g (400 mmol) of acetone cyanhydrin and 12.1 g (120 mmol) of triethylamine were added to the above-prepared reaction solution, followed by stirring for one night. The reaction solution was concentrated under reduced pressure. The residue thus obtained was washed with 300 ml of ether in addition to distilled water and dried over anhydride sodium sulfate and concentrated under reduced pressure. The residue was separated out by silica gel column chromatography, whereby 38.7 g of (2RS,3S)-2-hydroxy-3-[N-(2-methyl-2-propyloxycarbonyl)amino]heptanenitrile was obtained.

Workup

  1. additionwere added to the above-prepared reaction solution
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customThe residue thus obtained
  4. washwas washed with 300 ml of ether in addition
  5. distillationto distilled water
  6. dry with materialdried over anhydride sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was separated out by silica gel column chromatography

Sources & evidence

ORD record
ord-d11f9b2b35454f68bcf0b9a184e1180e
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

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