Ethanolamine → 13-Oxa-6-azadispiro[4.1.5.2]tetradecane

HRID 276697

Reaction equation

HRID 276697 reaction equation
[NH2:1][C:2]1([C:7]([OH:9])=O)[CH2:6][CH2:5][CH2:4][CH2:3]1.O[CH2:11][C:12]1(N)[CH2:16][CH2:15][CH2:14][CH2:13]1.OCCN.C1(=O)CCCCC1>>[CH2:3]1[C:2]2([CH2:7][O:9][C:11]3([CH2:12][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 7967CyclohexanoneHCID 663071-Aminocyclopentanemethanol

Product 1

HCID 1831620513-Oxa-6-azadispiro[4.1.5.2]tetradecane

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 cyclohexanone according to Method B4a, Step 1 to give 6-aza-13-oxadispiro[4.1.5.2]tetradecane. The oxazolidine was reduced according to Method B4a, Step 2 to give 1-(cyclohexylamino)-1-(hydroxymethyl)cyclopentane. The substituted 2-hydroxyethylamine was reacted with SOCl2 according to Method B7b to 1-(cyclohexylamino)-1-(chloromethyl)cyclopentane. The 2-chloroethylamine was reacted with 2-methyl-4-nitrophenyl isocyanate according to Method C4a to afford 1-cyclohexyl-2-(2-methyl-4-nitrophenylimino)-3-oxa-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record
ord-7bef1cc01a3d4996981a202525be0abc
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Linked notes

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