Ethanolamine → 2-Isopropyl-1-aza-3,8-dioxaspiro[4.5]decane
Reaction equation
[CH3:1][C:2]1[CH:8]=C([N+]([O-])=O)C=C[C:3]=1N.C(NC1C=CC=CC=1)=O.[NH2:21][C:22]1([C:28]([OH:30])=O)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.NC1(C(OC)=O)CCOCC1.NC1(CO)CCOCC1.OCCN.C(=O)C(C)C>>[CH:2]([CH:8]1[O:30][CH2:28][C:22]2([CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[NH:21]1)([CH3:3])[CH3:1]Participants
Reactant 7
Product 1
Procedure
2-Methyl-4-nitroaniline was converted to the 2-methyl-4-nitroformanilide according to Method A3a, Step 1. The formanilide was converted to 2-methyl-4-nitrophenyl isocyanide dichloride according to Method A3a, Step 2. 4-Aminotetrahydro-2H-pyran4-carboxylic acid was converted to the methyl ester according to Method B1b, Step 1. Methyl 4-aminotetrahydro-2H-pyran-4-carboxylate was reduced to 4-amino-4-(hydroxymethyl)tetrahydro-2H-pyran according to Method B1b, Step 2. The 2-hydroxyethylamine was reacted with isobutyraldehyde according to Method B4c, Step 1 to afford 2-isopropyl-1-aza-3,8-dioxaspiro[4.5]decane. The oxazolidine was reduced to 4-isobutylamino-4-(hydroxymethyl)tetrahydro-2H-pyran. The substituted 2-hydroxyethylamine was converted to 4-isobutylamino-4-(acetylthiomethyl)tetrahydro-2H-pyran according to Method C6c, Step 1. The thioacetate was saponified according to Method C6c, Step 2 to give 4-isobutylamino-4-(thiomethyl)tetrahydro-2H-pyran. The 2-thioethylamine was reacted with 2-methyl-4-nitrophenyl isocyanide dichloride to afford 2-(2-methyl-4-nitrophenylimino-1-isobutyl-1-aza-8-oxa-3-thiaspiro[4.5]decane.
Sources & evidence
- ORD record
- ord-89c892c1737547bb9abb0816d5253685
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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