Ethanolamine → 2-Isopropyl-1-aza-3,8-dioxaspiro[4.5]decane

HRID 276658ノート

反応式

HRID 276658 の反応式
[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]

参加物

8

反応物 7

HCID 700EthanolamineHCID 6561IsobutyraldehydeHCID 74412-Methyl-4-nitroanilineHCID 7671FormanilideHCID 27344014-aminotetrahydro-2H-pyran-4-carboxylic acidHCID 18316484(4-Aminooxan-4-yl)methanolHCID 18698314Methyl 4-aminooxane-4-carboxylate

生成物 1

HCID 183163232-Isopropyl-1-aza-3,8-dioxaspiro[4.5]decane

実験手順

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.

出典と根拠

ORDレコード
ord-89c892c1737547bb9abb0816d5253685
出典データセット
uspto-grants-2002_03
特許番号
US06353006B1

反応ノート

読み込み中…