Phthalimide → Undec-10-en-1-amine

HRID 47153

Reaction equation

[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].C1(=O)[NH:17]C(=O)C2=CC=CC=C12.NN>>[NH2:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

Reactant 3

HCID 6809Phthalimide

HCID 818510-Undecen-1-ol

HCID 9321Hydrazine

Product 1

HCID 11768976Undec-10-en-1-amineYield 66%

Procedure

Compound XXXI was prepared as described in Scheme I from 10-undecen-1-ol, 1, by a three step procedure in an overall yield of 31%. Alkylation of phthalimide with alkanol, 1, under Mitsunobu conditions, followed by reaction with hydrazine gave 1-aminoundec-10-ene, 2, in 66% yield. The amine was derivatized with O-acetylsalicyloyl chloride and the resulting alkene, 3, was oxidized to the acid using potassium permanganate. Removal of the acetate, followed by acid precipitation provided compound XXXI in 47% yield based on amine 2.

Sources & evidence

ORD record: ord-cd494bcf36924a318712597b682c1800
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699467B2

Linked notes

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