4-(1-Azidotridecyl)-2-triethylsilylfuran → 4-(1-Aminotridecyl)-2-triethylsilylfuran

HRID 1492938Notes

Reaction equation

HRID 1492938 reaction equation
[N:1]([CH:4]([C:17]1[CH:18]=[C:19]([Si:22]([CH2:27][CH3:28])([CH2:25][CH3:26])[CH2:23][CH3:24])[O:20][CH:21]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[NH2:1][CH:4]([C:17]1[CH:18]=[C:19]([Si:22]([CH2:27][CH3:28])([CH2:25][CH3:26])[CH2:23][CH3:24])[O:20][CH:21]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 194331464-(1-Azidotridecyl)-2-triethylsilylfuranHCID 21226445Aluminium lithium hydride

Product 1

HCID 150370864-(1-Aminotridecyl)-2-triethylsilylfuran

Procedure

Reacting 4-(1-hydroxytridecyl)-2-trimethylsilylfuran with diphenylphosphonyl azide and diethyl azidocarboxylate gives 4-(1-azidotridecyl)-2-triethylsilylfuran. Reducing this azide with lithium aluminum hydride gives 4-(1-aminotridecyl)-2-triethylsilylfuran. Acetylation of this intermediate with acetic anhydride gives 4-(1-acetamido)tridecyl-2-triethylsilylfuran. Oxidizing this amide with oxygen using Rose Bengal as an initiator gives 4-(1-acetamido)-5-hydroxy-2(5H)-furanone. Reduction of this furanone with sodium borohydride gives 4-(1-acetamido)-2(5H)-furanone.

Sources & evidence

ORD record
ord-5523ed214df44af4a26b63e748fea057
Source dataset
uspto-grants-1994_12
Patent number
US05376676

Reaction notes

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