(+-)-3-Quinuclidinol → HCID 13282599, compound

HRID 1388282Notes

Reaction equation

HRID 1388282 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[N:19]12[CH2:26][CH2:25][CH:22]([CH2:23][CH2:24]1)[CH:21](O)[CH2:20]2>>[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([OH:10])[C:7]([O:9][CH:21]2[CH:22]3[CH2:25][CH2:26][N:19]([CH2:24][CH2:23]3)[CH2:20]2)=[O:8])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 15381(+-)-3-QuinuclidinolHCID 13282597HCID 13282597, compound

Product 1

HCID 13282599HCID 13282599, compound

Procedure

The 4-aminobenzil may be prepared according to the method of Augl et al, Annu. Conf., SPE, Reinf. Plastic/Compos. Div. Proc., 26th, 19D, 1 (1971). The 4-aminobenzil is rearranged to yield 4-aminobenzilic acid which is in turn esterfied to produce the ethyl ester. The ethyl ester of the 4-aminobenzilic acid is then reacted with quinuclidin-3-ol to give the expected 3-quinuclidinyl 4-aminobenzilate (4-amino-QNB). The purified 4-amino-QNB is then converted to the 4-triazeno-QNB according to the procedure reported by Tewson et al, J. Nucl. Med. 20, 671 (1979). The purified 4-triazeno-QNB is then reacted with iodide or a desired gamma-emitting radionuclide to produce the desired product.

Sources & evidence

ORD record
ord-b700dc602e784be89fd368e791ccc348
Source dataset
uspto-grants-1984_02
Patent number
US04431627

Reaction notes

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