Diisobutylaluminum hydride → (3R)-3-(dibenzylamino)cyclopentanecarbaldehyde

Temperature

-78 °C

A solution of (3R)-3-(dibenzylamino)-N-methoxy-N-methylcyclopentanecarboxamide (3.34 g, 9.48 mmol) in THF (70 mL) was cooled to about −78° C., followed by the drop-wise addition of DIBAL-H (1.0 M in hexanes, 9.48 mL, 9.48 mmol). The reaction mixture was stirred at about −78° C. for about 1 h, and was quenched by drop-wise addition of saturated aqueous sodium potassium tartrate. The resulting mixture was stirred at room temperature for about 1 h. The solvent was removed under reduced pressure and the aqueous layer was extracted with EtOAc (100 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by chromatography on neutral alumina eluting with a gradient of 0-20% EtOAc in heptane to yield (3R)-3-(dibenzylamino)cyclopentanecarbaldehyde (1.63 g, 75%) as a colorless oil: LC/MS (Table 2, Method a) Rt=2.03 min; MS m/z: 294 (M+H)+.

1. customwas quenched by drop-wise addition of saturated aqueous sodium potassium tartrate
2. stirringThe resulting mixture was stirred at room temperature for about 1 h
3. customThe solvent was removed under reduced pressure
4. extractionthe aqueous layer was extracted with EtOAc (100 mL)
5. washThe organic layer was washed with brine
6. dry with materialdried over anhydrous MgSO4
7. concentrationconcentrated in vacuo
8. customThe residue was purified by chromatography on neutral alumina eluting with a gradient of 0-20% EtOAc in heptane

ORD record

ord-23131151cfd84731a5990e3104602f3b

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365579B2