HCID 118390034, compound → 1810076-94-8

HRID 1477971Notes

Reaction equation

HRID 1477971 reaction equation
[OH:1][CH:2]1[C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[O:1]=[C:2]1[C:6]2([CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1

Participants

4

Reactant 2

HCID 118390034HCID 118390034, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 1183900101810076-94-8Yield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-hydroxy-2-azaspiro[4.4]nonane-2-carboxylate (10.87 g, 45.04 mmol) in DCM (200 mL) were added 4 Å molecular sieve (20.00 g) followed by PCC (24.27 g, 112.6 mmol) slowly and the mixture was stirred at rt overnight. The resulting mixture was filtered and the filter cake was washed with EtOAc (50 mL×3). The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/50 to 1/10) to give the product as a white solid (8.56 g, 79.4%).

Workup

  1. filtrationThe resulting mixture was filtered
  2. washthe filter cake was washed with EtOAc (50 mL×3)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/50 to 1/10)

Sources & evidence

ORD record
ord-7dff9203dcc04dff9da314eb69e19fb9
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

Loading…