(S)-3-(Boc-amino)-2,4-dimethyl-2-pentanol

Base Information

• Chemical Name: (S)-3-(Boc-amino)-2,4-dimethyl-2-pentanol
• CAS No.: 157035-77-3
• Molecular Formula: C12H25NO3
• Molecular Weight: 231.33200
• Hs Code.: 2924199090
• European Community (EC) Number: 693-942-2
• DSSTox Substance ID: DTXSID50435702
• Nikkaji Number: J602.609E
• Wikidata: Q76415130
• Mol file: 157035-77-3.mol

Synonyms:(S)-3-(Boc-amino)-2,4-dimethyl-2-pentanol;157035-77-3;TERT-BUTYL N-[(3S)-2-HYDROXY-2,4-DIMETHYLPENTAN-3-YL]CARBAMATE;SCHEMBL1369971;DTXSID50435702;AWLRFWWWKJXWTQ-VIFPVBQESA-N;((S)-2-hydroxy-1-isopropyl-2-methyl-propyl)-carbamic acid tert-butyl ester;EN300-6967323;(S)-3-(Boc-amino)-2,4-dimethyl-2-pentanol, 97%;(S)-2,4-Dimethyl-3-(tert-butoxycarbonylamino)-2-pentanol

Chemical Property of (S)-3-(Boc-amino)-2,4-dimethyl-2-pentanol

Chemical Property:

• Melting Point: 54-60°C
• Flash Point: >110℃
• PSA: 62.05000
• LogP: 2.51100
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 231.18344366
• Heavy Atom Count: 16
• Complexity: 241

Purity/Quality:

(S)-3-(Boc-amino)-2,4-dimethyl-2-pentanol 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25-52/53
• Safety Statements: 45-61

MSDS Files:

Useful:

• Canonical SMILES: CC(C)C(C(C)(C)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)[C@@H](C(C)(C)O)NC(=O)OC(C)(C)C
• Uses: (S)-3-(Boc-amino)-2,4-dimethyl-2-pentanol can be used as an intermediate to prepare:Tris(4S-isopropyl-5,5-dimethyl-2-oxazolinyl)phenylborate ligand, applicable in the synthesis of various metal complexes bearing catalyst properties.Hydroxy isocyanides, important building blocks for the synthesis of (hydroxyalkyl)oxazoline ligands.

Technology Process of (S)-3-(Boc-amino)-2,4-dimethyl-2-pentanol

There total 2 articles about (S)-3-(Boc-amino)-2,4-dimethyl-2-pentanol 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: 11.0%

methylmagnesium bromide (75-16-1) + N-tert-butoxycarbonyl-L-valine methyl ester (58561-04-9) → tert-butyl (S)-(2-hydroxy-2,4-dimethylpentan-3-yl)carbamate (157035-77-3) + (3S)-3-N-(tert-butyloxycarbonyl)amino-4-methylpentan-2-one (128211-52-9,327600-47-5)

Guidance literature:

In tetrahydrofuran; 1.) 0 deg C, 2.) r.t., 20 h;

DOI:10.1021/jo00095a052

Reference yield: 2.0%

methylmagnesium bromide (75-16-1) + N-tert-butoxycarbonyl-L-valine methyl ester (58561-04-9) → tert-butyl (S)-(2-hydroxy-2,4-dimethylpentan-3-yl)carbamate (157035-77-3) + (RS)-N-(t-Butylcarboxy)-3-amino-4-methylpentan-2-one (327600-47-5)

Guidance literature:

In tetrahydrofuran; diethyl ether; for 36h; Ambient temperature;

DOI:10.1055/s-1998-1700

Reference yield:

tert-butyl (S)-(2-hydroxy-2,4-dimethylpentan-3-yl)carbamate (157035-77-3) → (E)-3-(4-{[Benzyl-((S)-1-isopropyl-2-methyl-allyl)-amino]-methyl}-phenyl)-acrylic acid (E)-3-(4-{[benzyl-((S)-1-isopropyl-2-methyl-allyl)-amino]-methyl}-phenyl)-acryloyloxymethyl ester

Guidance literature:

Multi-step reaction with 6 steps

1.1: 98 percent / HCl / ethyl acetate / 16 h / 20 °C

2.1: MgSO₄ / CH₂Cl₂ / 24 h / 20 °C

3.1: NaBH₄ / methanol / 24 h / 20 °C

4.1: NaH / dimethylformamide / 6 h / 20 °C

4.2: 70 percent / dimethylformamide / 16 h / 20 °C

5.1: 74 percent / Et₃N; hydroquinone / CH₂Cl₂ / 2 h / 0 °C

6.1: 46 percent / tetra-n-butylammonium chloride; NaHCO₃ / Pd(OAc)2 / 16 h / 110 °C

With hydrogenchloride; sodium tetrahydroborate; tetrabutyl-ammonium chloride; sodium hydride; sodium hydrogencarbonate; magnesium sulfate; triethylamine; hydroquinone; palladium diacetate; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/chem.200400608

upstream raw materials:

methylmagnesium bromide

N-tert-butoxycarbonyl-L-valine methyl ester

Downstream raw materials:

(S)-3-amino-2,4-dimethylpentan-2-ol

(S)-3-(4-Iodo-benzylamino)-2,4-dimethyl-pentan-2-ol

(S)-3-[Benzyl-(4-iodo-benzyl)-amino]-2,4-dimethyl-pentan-2-ol

Acrylic acid (S)-2-[benzyl-(4-iodo-benzyl)-amino]-1,1,3-trimethyl-butyl ester