56267-48-2 | tert-Butyl furan-3-ylcarbamate

Packsize	Purity	Availability	Price	Discounted Price
250mg	97%	in stock	$13.00	$9.00
1g	97%	in stock	$18.00	$12.00
5g	97%	in stock	$53.00	$37.00

Description

• Catalog Number: AB49134
• Chemical Name: tert-Butyl furan-3-ylcarbamate
• CAS Number: 56267-48-2
• Molecular Formula: C9H13NO3
• Molecular Weight: 183.2044
• MDL Number: MFCD09839085
• SMILES: O=C(OC(C)(C)C)Nc1cocc1

Computed Properties

• Complexity: 186
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 13
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 3
• XLogP3: 1.6

Upstream Synthesis Route

The upstream synthesis route for tert-Butyl furan-3-ylcarbamate involves several key steps starting from furan:

1. **Hydroxylation of Furan**: Furan is hydroxylated at the 3-position to form furan-3-ol via electrophilic addition using reagents like m-CPBA (meta-Chloroperoxybenzoic acid) or singlet oxygen in the presence of a sensitizer.

2. **Protection of Hydroxyl Group**: The hydroxyl group of furan-3-ol is protected by conversion to a silyl ether using a silyl chloride, such as tert-butyldimethylsilyl chloride (TBDMS-Cl), in the presence of a base like imidazole, to form 3-(tert-butyldimethylsilyloxy)furan.

3. **Formation of Isocyanate**: A suitable amine, such as tertiary-butylamine, is reacted with phosgene to form tert-butyl isocyanate in a strictly controlled environment, as phosgene is highly toxic and reactive.

4. **Deprotection and Carbamation**: The silyl ether protected furan is then deprotected under acidic conditions to regenerate the furan-3-ol, which is immediately reacted with the previously synthesized tert-butyl isocyanate to form the target product, tert-Butyl furan-3-ylcarbamate.

Throughout each step, careful control of reaction conditions including temperature, stoichiometry, and use of inert atmosphere when necessary, is vital. Purification techniques such as extraction, column chromatography, or recrystallization may be utilized to isolate and purify intermediates and the final product.