Ammonia → 2-{Bicyclo[2.2.1]heptan-2-yl}ethan-1-amine

Reaction equation

[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9](O)=O.O=S(Cl)Cl.[NH3:16].[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][CH2:9][NH2:16]

Participants

Reactant 4

HCID 222Ammonia

HCID 24386Thionyl Chloride

HCID 79139Norborn-2-ylacetic acid

HCID 21226445Aluminium lithium hydride

Product 1

HCID 202228702-{Bicyclo[2.2.1]heptan-2-yl}ethan-1-amineYield 35%

Procedure

Norbornane-2-acetic acid was treated with SOCl2, then with NH3. The resulting amine was reduced with LiAlH4 to give the desired intermediate. Yield: 35%.

Sources & evidence

ORD record: ord-89ff04e69db24ab5aa91db85b2fdded3
Source dataset: uspto-grants-1987_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04634701

Reaction notes

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