Dimethylformamide → HCID 86649018, compound

HRID 1367466Notes

Reaction equation

HRID 1367466 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C:9](=[O:11])[CH2:8][C@H:7]1[C:12](=[O:17])[NH:13][CH2:14][C:15]#[N:16])=[O:5])[CH3:2].CN(C=O)C.[BH4-].[Na+]>C1COCC1>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C@H:9]([OH:11])[CH2:8][C@H:7]1[C:12](=[O:17])[NH:13][CH2:14][C:15]#[N:16])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4311764Sodium borohydrideHCID 86649017HCID 86649017, compound

Product 1

HCID 86649018HCID 86649018, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of (1R,2R)-2-(cyanomethyl-carbamoyl)-4-oxo-cyclopentanecarboxylic acid ethyl ester (2.7 mmol) in THF (12 ml) was added DMF (1 ml), the solution was cooled to 0° C., sodium borohydride (3.3 mmol) was added and stirring was continued for 2 h. The mixture was partitioned between 1N aqueous HCl and ethyl acetate, the organic layer was dried, evaporated and the residue chromatographed on silica using dichloromethane/MeOH (97:3) to give in the first fraction (1R,2R,4R)-2-(cyanomethyl-carbamoyl)-4-hydroxy-cyclopentanecarboxylic acid ethyl ester as a white solid. MS: 241.4 (M+H)+. The second fraction contained the desired isomer,

Workup

  1. customThe mixture was partitioned between 1N aqueous HCl and ethyl acetate
  2. customthe organic layer was dried
  3. customevaporated
  4. customthe residue chromatographed on silica

Sources & evidence

ORD record
ord-88058659d051422faeebefb41ccbaee5
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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