HCID 117702498, compound → HCID 117702617, compound

HRID 1503255Notes

Reaction equation

HRID 1503255 reaction equation
[OH:1][CH2:2][C:3]12[CH2:10][C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([CH2:8][CH2:9]1)[CH2:6][CH2:5][CH2:4]2.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH:2]([C:3]12[CH2:10][C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])([CH2:8][CH2:9]1)[CH2:6][CH2:5][CH2:4]2)=[O:1]

Participants

4

Reactant 2

HCID 117702498HCID 117702498, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 117702617HCID 117702617, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 5-(hydroxymethyl)bicyclo[3.2.1]octan-1-ylcarbamate (7.0 g, 24.8 mmol) in DCM (50 mL) was added PCC (8.0 g, 37.2 mmol) in portions under N2 and the reaction mixture was stirred at room temperature for two hours. The mixture was filtered through a pad of silica gel and the filtrate was concentrated under reduced pressure to give 6.44 g (92%) of the crude title compound, tert-butyl 5-formylbicyclo[3.2.1]octan-1-ylcarbamate, as a brown oil, which was used in the next step without further purification. ESI-MS m/z: 198 (M-55)+.

Workup

  1. filtrationThe mixture was filtered through a pad of silica gel
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4cf437fc9c714b18a9a3a11272b939e5
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

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