101376-25-4

Basic information

• Product Name: 3(S)-HYDROXYMETHYL-4-BENZYLMORPHOLINE
• Synonyms: (S)-4-BENZYL-3-HYDROXYMETHYLMORPHOLINE;(S)-(4-benzylMorpholin-3-yl)Methanol;(3S)-4-(Phenylmethyl)-3-morpholinemethanol;(S)-4-(phenylmethyl)-3-Morpholinemethanol;(4-Benzyl-3-Morpholinyl)Methanol (4Benzylmorpholin3yl)methanol;(3S)-4-(Phenylmethyl)-3-morpholinemethanol,99%e.e.
• CAS NO: 101376-25-4
• Molecular Formula: C₁₂H₁₇NO₂
• Molecular Weight: 207.27
• Mol File: 101376-25-4.mol

Chemical Properties

• Melting Point: 230-231 °C(Solv: ethanol (64-17-5); ethyl ether (60-29-7))
• Boiling Point: 322.7 °C at 760 mmHg
• Flash Point: 149 °C
• Appearance: /
• Density: 1.117 g/cm³
• Vapor Pressure: 0.000113mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 14.85±0.10(Predicted)
• CAS DataBase Reference: 3(S)-HYDROXYMETHYL-4-BENZYLMORPHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3(S)-HYDROXYMETHYL-4-BENZYLMORPHOLINE(101376-25-4)
• EPA Substance Registry System: 3(S)-HYDROXYMETHYL-4-BENZYLMORPHOLINE(101376-25-4)

Safety Data

• Hazardous Substances Data: 101376-25-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3(S)-HYDROXYMETHYL-4-BENZYLMORPHOLINE is used as a key intermediate in the synthesis of non-stimulant appetite suppressants. Unlike conventional appetite suppressants, this compound does not release neurotransmitters, making it a potentially safer and more effective alternative for weight management and obesity treatment.

InChI:InChI=1/C12H17NO2/c14-9-12-10-15-7-6-13(12)8-11-4-2-1-3-5-11/h1-5,12,14H,6-10H2/t12-/m0/s1

Upstream product

• 106910-77-4 N-(phenylmethyl)-D-serine 
• 100-52-7 benzaldehyde 
• 106973-36-8 (3R)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid 

Downstream Products

• 913719-06-9 (3S)-3-(3-phenylprop-2-yn-1-yl)morpholine 
• 211053-50-8 (S)-3-(hydroxymethyl)morpholine 
• 101376-23-2 (S)-3-<(benzyloxy)methyl>-4-(phenoxycarbonyl)morpholine 
• 101376-27-6 (S)-3-<(benzyloxy)methyl>morpholine 
• 218595-25-6 (3S)-3-methoxymethylmorpholine 

Relevant articles and documents

A Conformational Restriction Strategy for the Identification of a Highly Selective Pyrimido-pyrrolo-oxazine mTOR Inhibitor

The mechanistic target of rapamycin (mTOR) plays a pivotal role in growth and tumor progression and is an attractive target for cancer treatment. ATP-competitive mTOR kinase inhibitors (TORKi) have the potential to overcome limitations of rapamycin derivatives in a wide range of malignancies. Herein, we exploit a conformational restriction approach to explore a novel chemical space for the generation of TORKi. Structure-activity relationship (SAR) studies led to the identification of compound 12b with a ～450-fold selectivity for mTOR over class I PI3K isoforms. Pharmacokinetic studies in male Sprague Dawley rats highlighted a good exposure after oral dosing and a minimum brain penetration. CYP450 reactive phenotyping pointed out the high metabolic stability of 12b. These results identify the tricyclic pyrimido-pyrrolo-oxazine moiety as a novel scaffold for the development of highly selective mTOR inhibitors for cancer treatment.

Fused Thiazole Derivatives As Kinase Inhibitors

A series of 6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5H)-one derivatives, which are substituted in the 2-position by a substituted morpholin-4-yl moiety, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

FUSED THIAZOLE AND THIOPHENE DERIVATIVES AS KINASE INHIBITORS

A series of fused bicyclic thiazole and thiophene derivatives which are substituted in the 2-position by an optionally substituted morpholin-4-yl moiety, and in the 4-position by hydroxy, oxo or an amine moiety, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions. (I)

THIAZOLE DERIVATIVES AS KINASE INHIBITORS

A series of thiazole derivatives which are substituted in the 2-position by a substituted morpholin-4-yl moiety, being selective inhibitors of P13 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

FUSED THIAZOLE DERIVATIVES AS KINASE INHIBITORS

A series of 6,7-dihydro[1,3]thiazolo[5,4-c]pyridin-4(5H)-one derivatives, which are substituted in the 2-position by a substituted morpholin-4-yl moiety, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

2-AMINOBENZOXAZOLE CARBOXAMIDES AS 5HT3 MODULATORS

Compounds of formulae I, II and III: are disclosed as 5-HT3 inhibitors. The compounds are useful in treating CINV, IBS-D and other diseases and conditions.

FUSED THIAZOLE DERIVATIVES AS KINASE INHIBITORS

A series of 5,6-dihydro-l,3-benzothiazol-7(4H)-one derivatives, and analogues thereof, which are substituted in the 2-position by an optionally substituted morpholin-4-yl moiety, being selective inhibitors of PD kinase enzymes, are accordingly of b.enefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

Chiral Synthesis of 3-Substituted Morpholines via Serine Enantiomers and Reductions of 5-Oxomorpholine-3-carboxylates

The chiral synthesis of 3-hydroxymethyl- and 3-carboxy-morpholines from serine enantiomers is described.Chemoselective and total reductions of 5-oxomorpholine-3-carboxylates are key synthetic steps.