Acetone Cyanohydrin → HCID 86596973, compound

HRID 2225299Notes

Reaction equation

HRID 2225299 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([C:27](OCC)=O)=NC(OCC)=O.[CH2:32]([N:39]([CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C@H:40]1[CH2:45][CH2:44][C@@H:43]([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[CH2:42][C@H:41]1[CH2:54]O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CC(C)(O)C#N>C1COCC1>[C:27]([CH2:54][C@H:41]1[C@@H:40]([N:39]([CH2:56][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:45][CH2:44][C@@H:43]([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[CH2:42]1)#[N:20]

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86596972HCID 86596972, compound

Product 1

HCID 86596973HCID 86596973, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
-20 °C

Procedure

Examples 11p and 11q, Step 4: To a solution of triphenylphosphine (4.47 g, 17.04 mmoles) in 50 ml of anhydrous THF at −20° C. was added 7.41 ml of 40% solution of diethyl azodicarboxylate in THF (17.04 mmoles) dropwise, and the mixture was stirred for 20 minutes at −20° C. Then to the mixture was added a solution of tert-butyl (1R,3R,4S)-4-(dibenzylamino)-3-(hydroxymethyl)cyclohexylcarbamate (1.81 g, 4.26 mmoles) in 20 ml of anhydrous THF, and it was stirred for 20 minutes at −20° C. At the end of the stirring was added 20 ml of anhydrous THF followed by acetone cyanohydrine (1.56 ml, 17.04 mmoles), and it was continued to stir for 1.5 hours while gradually raising the temperature to 8° C. The reaction was quenched by several drops of methanol, and the solvent was evaporated off. The residue was purified by column chromatography (silica gel, 25:75 EtOAc and hexane) to give 1.87 g of tert-butyl (1R,3S,4S)-3-(cyanomethyl)-4-(dibenzylamino)cyclohexylcarbamate.

Workup

  1. stirringwas stirred for 20 minutes at −20° C
  2. stirringto stir for 1.5 hours
  3. temperaturewhile gradually raising the temperature to 8° C
  4. customThe reaction was quenched by several drops of methanol
  5. customthe solvent was evaporated off
  6. customThe residue was purified by column chromatography (silica gel, 25:75 EtOAc and hexane)

Sources & evidence

ORD record
ord-d8953bbaf50d4d53ba1a94d885adecd6
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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