Ethanolamine → 13-aza-6-oxadispiro[4.2.4.I]tridecane

HRID 276699

Reaction equation

HRID 276699 reaction equation
[NH2:1][C:2]1([C:7]([OH:9])=O)[CH2:6][CH2:5][CH2:4][CH2:3]1.OC[C:12]1(N)[CH2:16][CH2:15][CH2:14][CH2:13]1.OCCN.C1(=O)CCCC1>>[CH2:3]1[C:2]2([CH2:7][O:9][C:12]3([CH2:16][CH2:15][CH2:14][CH2:13]3)[NH:1]2)[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 4

HCID 700EthanolamineHCID 2901CycloleucineHCID 8452CyclopentanoneHCID 663071-Aminocyclopentanemethanol

Product 1

HCID 1831628713-aza-6-oxadispiro[4.2.4.I]tridecane

Procedure

1-Aminocyclopentanecarboxylic acid was converted to the methyl ester according to Method B1c, Step 1. The ester reduced to 1-hydroxymethylcyclopentanamine according to Method B1c, Step 2. The hydroxyethylamine was reacted with cyclopentanone according to Method B4d, Step 1 to give 6-aza-12-oxadispiro[4.1.4.2]tridecane. The oxazolidine was reduced according to Method B4d, Step 2 to give 1-(cyclopentylamino)-1-(hydroxymethyl)cyclopentane. 4-Amino-3-ethylbenzonitrile was converted to 4-cyano-2-ethylformanilide according to Method A3a, Step 1. The formanilide was reacted with SOCl2 and SO2Cl2 according to Method A3a, Step 2 to give 4-cyano-2-ethylphenyl isocyanide dichloride. The substituted 2-hydroxyethylamine was reacted with 2-methyl-4-nitrophenyl isocyanide dichloride according to Method C7a to afford 1-cyclopentyl-2-(2-methyl-4-nitrophenylimino)-3-oxa-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record
ord-24f06a743e17471ba859c15d2e3ed75b
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Linked notes

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