tert-butyl N-[(1R,3S)-3-formylcyclopentyl]carbamate

Base Information

• Chemical Name: tert-butyl N-[(1R,3S)-3-formylcyclopentyl]carbamate
• CAS No.: 551964-49-9
• Molecular Formula: C11H19NO3
• Molecular Weight: 213.27346
• European Community (EC) Number: 877-686-0
• Mol file: 551964-49-9.mol

Synonyms:551964-49-9;tert-butyl N-[(1R,3S)-3-formylcyclopentyl]carbamate;tert-Butyl ((1R,3S)-3-formylcyclopentyl)carbamate;SCHEMBL3901035;AT10157;AT23237;3-BOC-AMINOCYCLOPENTANE-1-CARBALDEHYDE;EN300-657184;Z2887852040;rac-tert-butyl N-[(1R,3S)-3-formylcyclopentyl]carbamate

Chemical Property of tert-butyl N-[(1R,3S)-3-formylcyclopentyl]carbamate

Chemical Property:

• PSA: 55.40000
• LogP: 2.26960
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 213.13649347
• Heavy Atom Count: 15
• Complexity: 245

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CCC(C1)C=O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](C1)C=O

Technology Process of tert-butyl N-[(1R,3S)-3-formylcyclopentyl]carbamate

There total 3 articles about tert-butyl N-[(1R,3S)-3-formylcyclopentyl]carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

tert-butyl ((1R,3S)-3-(hydroxymethyl)cyclopentyl)carbamate (347185-68-6,167081-31-4,497159-95-2) → ((1R,3S)-3-formyl-cyclopentyl)-carbamic acid tert-butyl ester (551964-49-9)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; at -60 - -40 ℃; for 1h;

DOI:10.1016/j.bmcl.2004.04.036

Reference yield:

(1S,3R)-3-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid (261165-05-3) → ((1R,3S)-3-formyl-cyclopentyl)-carbamic acid tert-butyl ester (551964-49-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NMM / tetrahydrofuran / 0.75 h / -15 °C

2: NaBH₄ / H₂O; tetrahydrofuran / 2 h / 0 - 20 °C

3: 75 percent / oxalyl chloride; Et₃N; DMSO / 1 h / -60 - -40 °C

With 4-methyl-morpholine; sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; water; 3: Swern oxidation;

DOI:10.1016/j.bmcl.2004.04.036

Reference yield:

C16H27NO6 → ((1R,3S)-3-formyl-cyclopentyl)-carbamic acid tert-butyl ester (551964-49-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / H₂O; tetrahydrofuran / 2 h / 0 - 20 °C

2: 75 percent / oxalyl chloride; Et₃N; DMSO / 1 h / -60 - -40 °C

With sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; water; 2: Swern oxidation;

DOI:10.1016/j.bmcl.2004.04.036

upstream raw materials:

tert-butyl ((1R,3S)-3-(hydroxymethyl)cyclopentyl)carbamate

(1S,3R)-3-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid

Downstream raw materials:

3-(3-tert-butoxycarbonylamino-cyclopentyl)-3-(4-methoxy-benzylamino)-propionic acid tert-butyl ester

3-(3-tert-butoxycarbonylamino-cyclopentyl)-3-[tert-butoxycarbonyl-(4-methoxy-benzyl)-amino]-propionic acid tert-butyl ester