tert-butyl (1S,2R)-2-{[(cyanomethyl)amino]carbonyl}cyclohexylcarbamate → (1r,2s)-2-Amino-n-(cyanomethyl)cyclohexanecarboxamide

HRID 1593987Notes

Reaction equation

HRID 1593987 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]1[NH:13]C(=O)OC(C)(C)C)=[O:6])#[N:2]>C(O)=O>[NH2:13][C@H:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C@H:7]1[C:5]([NH:4][CH2:3][C:1]#[N:2])=[O:6]

Participants

3

Reactant 1

HCID 60098559tert-butyl (1S,2R)-2-{[(cyanomethyl)amino]carbonyl}cyclohexylcarbamate

Product 1

HCID 60098554(1r,2s)-2-Amino-n-(cyanomethyl)cyclohexanecarboxamideYield 59.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The nitrile compound of step 3 (5.82 g, 20.68 mmol) was dissolved in 69 mL (0.3M) of formic acid and stirred at room temperature for 5 h to completion. The formic acid was evaporated and the residue partitioned between ethyl acetate and 1 N sodium hydroxide, repeating the extraction three times with fresh ethyl acetate. The organic layers were combined, dried over magnesium sulfate and concentrated to give 2.22 g of the crude (1R,2S)-2-amino-N-(cyanomethyl)cyclohexanecarboxamide.

Workup

  1. customThe formic acid was evaporated
  2. customthe residue partitioned between ethyl acetate and 1 N sodium hydroxide
  3. extractionthe extraction three times with fresh ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a33712b3df144a369607f0266319e832
Source dataset
uspto-grants-2007_11
Patent number
US07300934B2

Reaction notes

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