Dimethylformamide → tert-butyl N-[(1S,3R)-3-(cyanomethyl)cyclopentyl]carbamate

HRID 352160Notes

Reaction equation

HRID 352160 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][CH2:11][CH:10]1COS(C1C=CC(C)=CC=1)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:26]#N.[Na+].C[N:30]([CH:32]=O)C>>[C:32]([CH2:26][C@@H:12]1[CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13]1)#[N:30]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 22713776n-[t-Butoxycarbonyl]-2-(p-toluenesulfonyloxymethyl)cyclopentylamine

Product 1

HCID 20729728tert-butyl N-[(1S,3R)-3-(cyanomethyl)cyclopentyl]carbamate

Conditions

Temperature
80 °C

Procedure

To a solution of 8.2 g (0.0222 mol) of N-[t-butoxycarbonyl]-2-(p-toluenesulfonyloxymethyl)cyclopentylamine in DMF (250 mL) was added 3.3 g (0.067 mmol) of NaCN and the suspension was heated at 80° C. for 4 h. The solvent was removed in vacuo at 40° C. and the residue was slurried in brine. The aqueous layer was extracted with ethyl acetate, dried and the solvent was removed in vacuo to yield 5.7 g of the title compound. MS(ES+)m/z=225. (one enantiomer)

Workup

  1. customThe solvent was removed in vacuo at 40° C.
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. customdried
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bbb6f2298eaa4684851d01a9ce39478a
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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