(S)-tert-Butyl 3-formyl-1-oxa-4-azaspiro[4.5]decane-4-carboxylate

Base Information

• Chemical Name: (S)-tert-Butyl 3-formyl-1-oxa-4-azaspiro[4.5]decane-4-carboxylate
• CAS No.: 168772-32-5
• Molecular Formula: C14 H23 NO4
• Molecular Weight: 269.341
• Hs Code.: 2934999090
• European Community (EC) Number: 803-094-9
• Nikkaji Number: J1.052.614K
• Mol file: 168772-32-5.mol

Synonyms:168772-32-5;(S)-tert-Butyl 3-formyl-1-oxa-4-azaspiro[4.5]decane-4-carboxylate;tert-butyl (3S)-3-formyl-1-oxa-4-azaspiro[4.5]decane-4-carboxylate;(S)-N-Boc-1-oxa-4-azaspiro[4.5]decane-3-carboxaldehyde;(S)-N-Boc-1-oxa-4-azaspiro[4.5]decane-3-carboxaldehyde, 95%;(4S)-3-(tert-Butyloxycarbonyl)spiro[oxazolidine-2,1'-cyclohexane]-4-carbaldehyde

Chemical Property of (S)-tert-Butyl 3-formyl-1-oxa-4-azaspiro[4.5]decane-4-carboxylate

Chemical Property:

• Melting Point: 54-59°C
• PSA: 55.84000
• LogP: 2.41950
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 269.16270821
• Heavy Atom Count: 19
• Complexity: 355

Purity/Quality:

(S)-N-Boc-1-oxa-4-azaspiro[4.5]decane-3-carboxaldehyde 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C(COC12CCCCC2)C=O
• Isomeric SMILES: CC(C)(C)OC(=O)N1[C@@H](COC12CCCCC2)C=O

Technology Process of (S)-tert-Butyl 3-formyl-1-oxa-4-azaspiro[4.5]decane-4-carboxylate

There total 3 articles about (S)-tert-Butyl 3-formyl-1-oxa-4-azaspiro[4.5]decane-4-carboxylate 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:

(3S)-3-hydroxymethyl-1-oxa-4-azaspiro<4,5>decane-4-carboxylic acid 4-tert-butyl ester (171623-05-5) → (S)-Garner's aldehyde (168772-32-5)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 1h;

DOI:10.1016/0040-4020(96)00672-2

Reference yield:

2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester (95715-85-8) → (S)-Garner's aldehyde (168772-32-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / TsOH*H₂O / benzene / 36 h / Heating

2: 92 percent / NaBH₄, LiCl / ethanol; tetrahydrofuran / 4 h / Ambient temperature

3: Dess-Martin periodinane / CH₂Cl₂ / 1 h

With sodium tetrahydroborate; Dess-Martin periodane; toluene-4-sulfonic acid; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; benzene;

DOI:10.1016/0040-4020(96)00672-2

Reference yield:

1-oxa-4-azaspiro<4,5>decane-(3R)-3,4-dicarboxylic acid 4-tert-butyl ester 3-methyl ester (171623-06-6) → (S)-Garner's aldehyde (168772-32-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / NaBH₄, LiCl / ethanol; tetrahydrofuran / 4 h / Ambient temperature

2: Dess-Martin periodinane / CH₂Cl₂ / 1 h

With sodium tetrahydroborate; Dess-Martin periodane; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/0040-4020(96)00672-2

upstream raw materials:

(3S)-3-hydroxymethyl-1-oxa-4-azaspiro<4,5>decane-4-carboxylic acid 4-tert-butyl ester

2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester

1-oxa-4-azaspiro<4,5>decane-(3R)-3,4-dicarboxylic acid 4-tert-butyl ester 3-methyl ester

Downstream raw materials:

(3S)-3-((1S)-1-hydroxyphenylmethyl)-1-oxa-4-azaspiro[4,5]decane-4-carboxylic acid tert-butyl ester

(2S,3R)-3-acetoxy-3-(4-benzyloxy-3-chlorophenyl)-2-tert-butoxycarbonylamino-1,2-cyclohexylidenepropan-1-ol

(2S,3S)-3-acetoxy-3-(4-benzyloxy-3-chlorophenyl)-2-tert-butoxycarbonylamino-1,2-cyclohexylidenepropan-1-ol

tert-butyl (1,3-dihydroxy-1-phenylpropan-2-yl)carbamate