Hydrochloric Acid → 1-Azabicyclo[2.2.2]octane-3-carboxaldehyde

HRID 1534884Notes

Reaction equation

CN(OC)[C:3]([CH:5]1[CH:10]2[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]2)[CH2:6]1)=[O:4].[H-].C([Al+]CC(C)C)C(C)C.Cl.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH:3]([CH:5]1[CH:10]2[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]2)[CH2:6]1)=[O:4]

Participants

Conditions

Temperature: -70 °C

Procedure

(±) 3-(N-Methyl-N-methoxyaminocarbonyl)-1-azabicyclo[2.2.2]octane (D31) (6.0g, 0.03 moles) was dissolved in dry toluene (250ml) and cooled to -70° C. under a nitrogen atmosphere. Diisobutylaluminium hydride (1.5M solution in toluene (45ml, 0.068 moles) was added dropwise. The reaction was then allowed to warm to room temperature over a period of 2h. Hydrochloric acid (2N, 300ml) was added rapidly with vigorous stirring. The aqueous layer was saturated with potassium carbonate and the mixture extracted with chloroform (3×250ml). The combined extracts were dried (Na2SO4) and evaporated to dryness. The residue was distilled in a Kugelrohr to yield the title compound (D32) as a colourless oil (3.6g, 85%) b.p. 100° C. at 1.0

Workup

temperatureto warm to room temperature over a period of 2h
extractionthe mixture extracted with chloroform (3×250ml)
dry with materialThe combined extracts were dried (Na2SO4)
customevaporated to dryness
distillationThe residue was distilled in a Kugelrohr

Sources & evidence

ORD record: ord-c08aef9c0db74fd89e3727c042ecc30d
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05091397

Reaction notes

Loading…