Tetrahydrofuran → Tert-butyl 3-formyl-8-azabicyclo(3.2.1)octane-8-carboxylate

HRID 1667307Notes

Reaction equation

[C:1]([CH:3]1[CH2:9][CH:8]2[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:5]([CH2:6][CH2:7]2)[CH2:4]1)#N.[H-].C([Al+]CC(C)C)C(C)C.[O:28]1CCCC1>>[CH:1]([CH:3]1[CH2:9][CH:8]2[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:5]([CH2:6][CH2:7]2)[CH2:4]1)=[O:28]

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 21225700Diisobutylaluminumhydride

HCID 53487658tert-Butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 57712307Tert-butyl 3-formyl-8-azabicyclo(3.2.1)octane-8-carboxylate

Procedure

tert-Butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate was reacted in the presence of diisobutyl aluminum hydride in tetrahydrofuran to produce tert-butyl 3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate.

Sources & evidence

ORD record: ord-0e237b6c623c4a71989b825c843b5696
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044206B2

Reaction notes

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