65376-05-8

Basic information

• Product Name: (1R,2R)-1,2-CYCLOHEXANEDIMETHANOL
• Synonyms: Lurasidone INT 3;[(1R,2R)-2-(hydroxymethyl)cyclohexyl]methanol;(1R,2R)-1,2-CYCLOHEXANEDI;(1R,2R)-1,2-Cyclohexanedimethanol;(1R,2R)-1,2-CYCLOHEXANEDIMETHANOL;(1R,2R)-cyclohexane-1,2-diyldimethanol;(1R,2R)-1,2-Bis(hydroxymethyl)cyclohexane;1,2-CyclohexanediMethanol, (1R,2R)-
• CAS NO: 65376-05-8
• Molecular Formula: C₈H₁₆O₂
• Molecular Weight: 144.21144
• EINECS: 1806241-263-5
• Product Categories: Miscellaneous Reagents
• Mol File: 65376-05-8.mol

Chemical Properties

• Melting Point: 63.0 to 67.0 °C
• Boiling Point: 270℃
• Flash Point: 129℃
• Appearance: /
• Density: 1.004
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.75±0.10(Predicted)
• CAS DataBase Reference: (1R,2R)-1,2-CYCLOHEXANEDIMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-1,2-CYCLOHEXANEDIMETHANOL(65376-05-8)
• EPA Substance Registry System: (1R,2R)-1,2-CYCLOHEXANEDIMETHANOL(65376-05-8)

Safety Data

• Hazardous Substances Data: 65376-05-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1R,2R)-1,2-Cyclohexanedimethanol is used as a chiral building block for the synthesis of complex organic molecules. Its unique stereochemistry allows for the creation of enantiomerically pure compounds, which are essential in the pharmaceutical industry for the development of drugs with fewer side effects and higher efficacy.
Used in Pharmaceutical Industry:
(1R,2R)-1,2-Cyclohexanedimethanol is used as a key intermediate in the development of pharmaceutical compounds. Its chiral nature enables the production of single-enantiomer drugs, which can have significant advantages over racemic mixtures in terms of safety, efficacy, and reduced side effects.
Used in Chemical Research:
(1R,2R)-1,2-Cyclohexanedimethanol serves as a valuable compound for research purposes in the field of chemistry. It can be used to study the effects of stereochemistry on the properties and reactivity of molecules, as well as to develop new synthetic methods and techniques for the preparation of chiral compounds.
Used in Material Science:
(1R,2R)-1,2-Cyclohexanedimethanol can be utilized in the development of new materials with specific properties, such as chiral polymers or materials with unique optical, electronic, or mechanical characteristics. Its application in this field can lead to the creation of innovative materials for various industries, including electronics, automotive, and aerospace.

Synthetic route

(1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester (140459-96-7) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
With hydrogen In methanol at 190℃; under 52505.3 Torr; Temperature; Pressure; Solvent;	94%
Stage #1: (1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester With diisobutylaluminium hydride In toluene at -5 - 20℃; for 6h; Inert atmosphere; Stage #2: With hydrogenchloride; water In toluene at -5 - 40℃; for 13h;	74%
With lithium aluminium tetrahydride In diethyl ether
Stage #1: (1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester With diisobutylaluminium hydride In toluene at 0 - 20℃; for 4h; Inert atmosphere; Stage #2: With hydrogenchloride In water at 0 - 40℃; for 18h;
With methanol; sodium tetrahydroborate In tetrahydrofuran at 40℃; for 3h; Temperature; Reflux;

(1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid (46022-05-3) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0℃; for 5h; Reflux;	88.4%
With Red-Al In tetrahydrofuran; toluene for 5h; Inert atmosphere; Reflux;	85.2%
Multi-step reaction with 2 steps 1: diethyl ether 2: LiAlH4 / diethyl ether View Scheme

(-)-(1R,2R)-trans-2-(hydroxymethyl)cyclohexanoic acid (65376-04-7) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 12h; Heating;	80%
With lithium aluminium tetrahydride

bis(D-menthyl) (1R,2R)-cyclohexane-1,2-dicarboxylate → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 19h; Inert atmosphere;	76%

(+/-)-trans-2-(hydroxymethyl)cyclohexylmethanol (76155-27-6) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
With C11H19NO

(+/-)-trans-2-(hydroxymethyl)cyclohexylmethanol (76155-27-6) → trans-2-(hydroxymethyl)cyclohexanecarboxylic acid (57280-65-6, 65376-04-7, 80795-84-2, 93379-40-9) + (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) + (1S,2S)-(–)-1,2-di(hydroxymethyl)cyclohexane (3205-34-3) + (-)-(1R,2R)-trans-2-(hydroxymethyl)cyclohexanoic acid (65376-04-7)

Conditions	Yield
With sodium hydroxide; NAD; silver nitrate; glycine; Flavin mononucleotide Product distribution; multistep reaction, other trans-diols, stereospecificity;

diethyl trans-1,2,3,6-tetrahydrophthalate (96946-89-3) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Stage #1: diethyl trans-1,2,3,6-tetrahydrophthalate With hydrogen; palladium on activated charcoal Stage #2: With lithium aluminium tetrahydride

(3aR,7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran-1-one (65376-03-6) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / H2 / Pd/C / methanol 2: 34 percent / NaOH / H2O / 192 h / 130 °C 3: 80 percent / LiAlH4 / diethyl ether / 12 h / Heating View Scheme

cis-1,2-cyclohexanedimethanol (15753-50-1) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / NAD+, FMN, pH 9, HLADH, NaOH, glycine / Ambient temperature 2: 34 percent / NaOH / H2O / 192 h / 130 °C 3: 80 percent / LiAlH4 / diethyl ether / 12 h / Heating View Scheme

cis-1,6-dihydroxymethyl-3-cyclohexene (439919-46-7) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 83 percent / NAD+, FMN, pH 9, HLADH, NaOH, glycine / 48 h / 20 °C 2: 86 percent / H2 / Pd/C / methanol 3: 34 percent / NaOH / H2O / 192 h / 130 °C 4: 80 percent / LiAlH4 / diethyl ether / 12 h / Heating View Scheme

(3aR,7aS)-hexahydroisobenzofuran-1-one (89395-29-9) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 34 percent / NaOH / H2O / 192 h / 130 °C 2: 80 percent / LiAlH4 / diethyl ether / 12 h / Heating View Scheme

1,2-cis-cyclohexanedicarboxylic anhydride (13149-00-3) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: LiAlH4 2: 80 percent / NAD+, FMN, pH 9, HLADH, NaOH, glycine / Ambient temperature 3: 34 percent / NaOH / H2O / 192 h / 130 °C 4: 80 percent / LiAlH4 / diethyl ether / 12 h / Heating View Scheme

phthalic acid dimethyl ester (131-11-3) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: Raney nickel; methanol / 50 - 60 °C / 73550.8 Torr / Hydrogenation.Behandeln des Reaktionsprodukts mit methanol. Natriummethylat 2: LiAlH4; diethyl ether 3: (1R)-menthyl isocyanate View Scheme

dimethyl cyclohexane-trans-1,2-dicarboxylate (3205-35-4) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4; diethyl ether 2: (1R)-menthyl isocyanate View Scheme

(x)C8H11N*C8H12O4 → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride / water 2.1: sulfuric acid / 18 h / 40 °C 3.1: diisobutylaluminium hydride / toluene / 6 h / -5 - 20 °C / Inert atmosphere 3.2: 13 h / -5 - 40 °C View Scheme

trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ethanol / 6.5 h / -70 - 20 °C / Resolution of racemate 2.1: hydrogenchloride / water 3.1: sulfuric acid / 18 h / 40 °C 4.1: diisobutylaluminium hydride / toluene / 6 h / -5 - 20 °C / Inert atmosphere 4.2: 13 h / -5 - 40 °C View Scheme
Multi-step reaction with 2 steps 1.1: ethanol / 30 h / 35 - 75 °C 1.2: 1 h 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 65 °C View Scheme
Multi-step reaction with 2 steps 1.1: (R)-1-phenyl-ethyl-amine / methanol; isopropyl alcohol / 30 - 40 °C 2.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 25 - 30 °C 2.2: 1 h View Scheme
Multi-step reaction with 4 steps 1: (R)-1-phenyl-ethyl-amine / methanol; isopropyl alcohol / 30 - 40 °C 2: tetrahydrofuran / 1 h / 25 - 30 °C 3: tetrahydrofuran / 45 - 50 °C 4: sodium tetrahydroborate; water / tetrahydrofuran / 1 h View Scheme

trans-cyclohex-4-ene-1,2-dicarboxylic acid (88-98-2, 2305-26-2, 15573-40-7, 50987-15-0, 51096-07-2, 51096-08-3) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: palladium; hydrogen / methanol / 30 - 35 °C 2.1: ethanol / 30 h / 35 - 75 °C 2.2: 1 h 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 65 °C View Scheme

racemic trans-cyclohexane-1,2-dicarboxylic acid → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: methanol / 0 - 35 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: Red-Al / tetrahydrofuran; toluene / 5 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 3 steps 1: (R)-1-phenyl-ethyl-amine / 5 °C 2: sulfuric acid / 4 h / Reflux 3: sodium tetrahydroborate; methanol / tetrahydrofuran / 3 h / 40 °C / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: diisopropylamine / ethanol / 3 h / -72 - 20 °C 2.1: sulfuric acid / 20 h / 10 - 50 °C 3.1: diisobutylaluminium hydride / toluene / 4 h / 0 - 20 °C / Inert atmosphere 3.2: 18 h / 0 - 40 °C View Scheme

(R,R)-1,2-cyclohexane dicarboxylic acid (R)-1-phenylethyl amine salt → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / 20 h / 10 - 50 °C 2.1: diisobutylaluminium hydride / toluene / 4 h / 0 - 20 °C / Inert atmosphere 2.2: 18 h / 0 - 40 °C View Scheme

dimethyl cis-1,2-cyclohexanedicarboxylate (1687-29-2) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium methylate / methanol / 4 h / Inert atmosphere; Reflux 1.2: 4 h / 75 °C / Inert atmosphere 1.3: 0 - 5 °C / pH 2 / Inert atmosphere 2.1: Red-Al / tetrahydrofuran; toluene / 5 h / Inert atmosphere; Reflux View Scheme

C16H16N4O6 → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 45 - 50 °C 2: sodium tetrahydroborate; water / tetrahydrofuran / 1 h View Scheme

((R,R)-cyclohexane-1,2-diyl)bis((1H-imidazol-1-yl)methanone) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8)

Conditions	Yield
With sodium tetrahydroborate; water In tetrahydrofuran for 1h;	15.5 g

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) + tert-butyldimethylsilyl chloride (18162-48-6) → ((1R,2R)-2-(((tert-butyldimethylsilyl)oxy)methyl)cyclohexyl)methanol (146611-58-7)

Conditions	Yield
Stage #1: (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane With n-butyllithium In tetrahydrofuran; cyclohexane at 0 - 20℃; for 3.25h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; cyclohexane at 20℃; for 1h; Inert atmosphere;	99%

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) → 8-oxabicyclo[4,3,0]nonane-7-one (2611-01-0)

Conditions	Yield
With (CH3)5C5*Ir(-OCH2C(C6H5)2NH-) In acetone at 20℃; for 36h;	98%

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) + p-methoxybenzyl chloride (824-94-2) → ((1R,2R)-2-{[(4-methoxybenzyl)oxy]methyl}cyclohexyl)methanol + C24H32O4

Conditions	Yield
Stage #1: (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane With sodium hydride In N,N-dimethyl-formamide; mineral oil at -20℃; for 0.5h; Inert atmosphere; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Inert atmosphere;	A 97% B 2%

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) → (1R,2R)-2-{[(4-methoxybenzyl)oxy]methyl}cyclohexanecarbaldehyde

Conditions	Yield
Stage #1: (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -60℃; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at -50 - 20℃; Inert atmosphere;	94%

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) + methanesulfonyl chloride (124-63-0) → (1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate (186204-35-3)

Conditions	Yield
With triethylamine at 0 - 5℃; Industrial scale;	92.6%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	92%
With triethylamine In chloroform at 0 - 20℃; for 5h;	90.8%

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) + p-toluenesulfonyl chloride (98-59-9) → (R)-trans-1,2-bis-(toluene-4-sulfonyloxymethyl)-cyclohexane (3205-36-5, 7436-01-3, 59461-66-4, 62208-94-0, 76155-28-7, 95810-29-0)

Conditions	Yield
With triethylamine In dichloromethane at -10 - 0℃; for 3h; Concentration;	92.5%

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) + C18H17N3O2S → C32H38N6O4S2

Conditions	Yield
Stage #1: (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane With sodium hydroxide In tetrahydrofuran Stage #2: C18H17N3O2S In tetrahydrofuran at 70℃; for 2h; Reagent/catalyst; Solvent; Temperature;	74%

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) + C18H17N3O2S → C20H27N3O3S

Conditions	Yield
Stage #1: (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane With sodium hydroxide In tetrahydrofuran Stage #2: C18H17N3O2S In tetrahydrofuran at -10℃;	32%

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) → trans-8-oxabicyclo[4.3.0]nonan-7-ol

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; dimethyl sulfoxide at 23℃; for 2h;

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) → ethyl (+/-)-(2E)-3-[(1RS,2SR)-2-(hydroxymethyl)-cyclohexyl]-2-propenoate

Conditions	Yield
Multi-step reaction with 2 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; H2O / 2 h / 23 °C 2: benzene / 16 h / Heating View Scheme

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) → ethyl (+/-)-(2E)-3-[(1RS,2SR)-2-(iodomethyl)cyclohexyl]-2-propenoate

Conditions	Yield
Multi-step reaction with 4 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; H2O / 2 h / 23 °C 2: benzene / 16 h / Heating 3: 94 percent / triethylamine / CH2Cl2 / 0 °C 4: 84 percent / sodium iodide / acetone / 14 h / Heating View Scheme

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) → ethyl (+/-)-(2E)-3-{(1RS,2SR)-2-[(methanesulfonyloxy)methyl]cyclohexane}-2-propenoate

Conditions	Yield
Multi-step reaction with 3 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; H2O / 2 h / 23 °C 2: benzene / 16 h / Heating 3: 94 percent / triethylamine / CH2Cl2 / 0 °C View Scheme

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) → (+/-)-(1RS,3aSR,7aSR)-1,3,3a,4,5,6,7,7a-octahydrobenzo[c]thiophene-1-acetic acid

Conditions	Yield
Multi-step reaction with 6 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; H2O / 2 h / 23 °C 2: benzene / 16 h / Heating 3: 94 percent / triethylamine / CH2Cl2 / 0 °C 4: 84 percent / sodium iodide / acetone / 14 h / Heating 5: 97 percent / ethanol / 120 h / Heating 6: 75 percent / potassium hydroxide; water / 8 h / Heating View Scheme

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) → (+/-)-(1SR,3aSR,7aSR)-1,3,3a,4,5,6,7,7a-octahydrobenzo[c]thiophene-1-acetic acid

Conditions	Yield
Multi-step reaction with 6 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; H2O / 2 h / 23 °C 2: benzene / 16 h / Heating 3: 94 percent / triethylamine / CH2Cl2 / 0 °C 4: 84 percent / sodium iodide / acetone / 14 h / Heating 5: 97 percent / ethanol / 120 h / Heating 6: 10 percent Chromat. / potassium hydroxide; water / 8 h / Heating View Scheme

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) → ethyl (+/-)-(1RS,3aSR,7aSR)-2-benzyl-2,3,3a,4,5,6,7,7a-octahydro-1H-isoindole-1-acetate

Conditions	Yield
Multi-step reaction with 5 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; H2O / 2 h / 23 °C 2: benzene / 16 h / Heating 3: 94 percent / triethylamine / CH2Cl2 / 0 °C 4: 84 percent / sodium iodide / acetone / 14 h / Heating 5: 70 percent / triethylamine / 120 h / Heating View Scheme

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) → (E)-3-((1R,2S)-2-Carbamimidoylsulfanylmethyl-cyclohexyl)-acrylic acid ethyl ester; hydriodide

Conditions	Yield
Multi-step reaction with 5 steps 1: o-iodoxybenzoic acid / dimethylsulfoxide; H2O / 2 h / 23 °C 2: benzene / 16 h / Heating 3: 94 percent / triethylamine / CH2Cl2 / 0 °C 4: 84 percent / sodium iodide / acetone / 14 h / Heating 5: 97 percent / ethanol / 120 h / Heating View Scheme

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8) → (3aR)-trans-octahydro-isobenzofuran (4743-54-8, 10479-79-5, 13149-01-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: aqueous KOH-solution View Scheme

Upstream product

• 76155-27-6 (+/-)-trans-2-(hydroxymethyl)cyclohexylmethanol 
• 65376-04-7 (-)-(1R,2R)-trans-2-(hydroxymethyl)cyclohexanoic acid 
• 140459-96-7 (1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester 
• 96946-89-3 diethyl trans-1,2,3,6-tetrahydrophthalate 
• 65376-03-6 (3aR,7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran-1-one 
• 131-11-3 phthalic acid dimethyl ester 
• 3205-35-4 trans dimethyl cyclohexane-1,2-dicarboxylate 
• 46022-05-3 (1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid 
• 88-98-2 trans-cyclohex-4-ene-1,2-dicarboxylic acid 
• 1687-29-2 dimethyl cis-1,2-cyclohexanedicarboxylate 
• 2305-32-0 trans-1,2-cyclohexanedicarboxylic acid 
• 13149-00-3 1,2-cis-cyclohexanedicarboxylic anhydride 
• 89395-29-9 (3aR,7aS)-hexahydroisobenzofuran-1-one 
• 439919-46-7 cis-1,6-dihydroxymethyl-3-cyclohexene 

Downstream Products

• 186204-35-3 (1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate 
• 367514-88-3 (3aR,4S,7R,7aS)-2-[((1R,2R)-2-{[4-(l1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl)methyl]hexahydro-1H-4,7-methanisoindol-1,3-dione hydrochloride 
• 146611-58-7 ((1R,2R)-2-(((tert-butyldimethylsilyl)oxy)methyl)cyclohexyl)methanol 

Relevant articles and documents

Fused-ring nitrogen and sulfur heterocycles by a tandem SN2-Michael addition reaction

A tandem SN2-Michael addition reaction has been developed for the synthesis of cis- and trans-fused nitrogen and sulfur heterocycles from the cis and trans isomers of ethyl (±)-(2E)-3-[2-(iodomethyl)cyclohexyl]-2-propenoate. Octahydro-1H-isoindole-1-acetic acid and octahydrobenzo[c]thiophene-1-acetic acid derivatives have been prepared and their stereochemistries elucidated using NMR and X-ray crystallographic methods. Cyclization substrates for both the cis- and the trans-fused rings are readily available in four steps from known compounds. Yields for the cyclization range from 80-85% and stereochemical selectivities with respect to the side chain vary from 12.5-16:1 for the cis-fused structures to 6-7.5:1 for the transfused structures. Steric interactions in the transition states for ring closure are proposed to rationalize the observed preferences.

Method for efficiently synthesizing 1R,2R-cyclohexanedimethanol by gas-solid phase technology

The invention discloses a method for efficiently synthesizing 1R,2R-cyclohexanedimethanol by a gas-solid phase technology. The method comprises the following steps: continuously inputting a 1R,2R-cyclohexanedicarboxylic acid and/or 1R,2R-cyclohexanedicarboxylic acid derivative solution into a continuous tubular reactor provided with a catalyst in a reducing atmosphere, and performing a continuousreaction at an air speed of 0.01-1000 g/g.h to obtain the 1R,2R-cyclohexanedimethanol. The method fully utilizes the characteristics of the gas-solid phase technology, and raw materials and the product only stay in the reaction system for a short time, so racemization of chiral compounds at a high temperature is effectively prevented, continuous production of 1R,2R-cyclohexanedimethanol is achieved, and the method is suitable for industrial production.

Preparation method for lurasidone hydrochloride

The invention discloses a preparation method for lurasidone hydrochloride. According to the preparation method, trans-1,2-cyclohexanedicarboxylic acid (SM-1) is used as a raw material and subjected to resolution, methyl esterification, reduction, methylsulfonylation, condensation, recrystallization and salt formation so as to eventually obtain lurasidone hydrochloride. The preparation method provided by the invention greatly reduces production cost and has the characteristics of high product yield, easy operation, low toxicity and suitability for industrial large-scale production.

A process for the preparation of intermediates [...] (by machine translation)

The invention relates to a process for the preparation of intermediates [...], the intermediate body is (3aR, 7aR) - 4 ˊ - (1,2-benzisothiazol-3-yl) eight hydrogen spiral [2H-isoindole -2,1 ˊ-piperazine] a sulfonate. The (1R, 2R) - 1,2-cyclohexane dimethanol as raw materials, dialkyltinacetal after armor is a sulfonic acid ester, with the 3 - (1-piperazinyl) - 1,2 benzothiazin hydrochloride reaction to obtain the required intermediate. (by machine translation)

AN IMPROVED PROCESS FOR THE PREPARATION OF LURASIDONE HYDROCHLORIDE

Disclosed herein is an improved process for the preparation of Lurasidone and its pharmaceutically acceptable salts via novel intermediate and use thereof for the preparation of an antipsychotic agent useful for the treatment of schizophrenia and bipolar disorder. Further, present invention provides a cost effective and eco-friendly process for producing Lurasidone hydrochloride of formula (I) substantially free of residual solvent(s) at industrial scale.

Truncated borrelidin analogues: Synthesis by sequential cross metathesis/olefination for the southern fragment and biological evaluation

The construction of novel borrelidin analogues is reported in which the northern fragment is truncated to a simple hydroxyundecanecarboxylate and the original cyclopentanecarboxylic acid in the southern fragment is replaced with different six-membered rings. The required precursors were prepared by cross metathesis of the appropriate carbocycle-based homoallylic alcohol with crotonaldehyde followed by HWE olefination of the resulting enal with bromocyanophosphonate. The key aldehyde for intramolecular cross coupling was accessible by oxidation of the hydroxy group of the linked undecanecarboxylate unit. Grignard mediated macrocyclization finally yielded the borrelidin related products. The investigation is complemented by SAR studies and quantum-chemical calculations.

Enantioselective Synthesis of ((1 R,2 R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate

A concise, economical, and highly enantioselective synthesis of bismesylate intermediate of lurasidone HCl, an antipsychotic, has been developed. The key steps involved in the synthesis are thionyl chloride-catalyzed esterification of tetrahydrophthalic anhydride in MeOH, epimerization of cis to trans isomer, hydrolysis of the diester, resolution of the diacid, reduction with Red-Al, and finally bismesylation of the corresponding diol, which provided the desired intermediate ((1 R,2 R)-cyclohexane-1,2-diyl)bis(methylene) dimethanesulfonate in overall good yield.

PROCESS FOR THE PREPARATION OF LURASIDONE HYDROCHLORIDE

Provided herein is a process for the preparation of the antipsychotic agent lurasidone hydrochloride useful for the treatment of schizophrenia.

PROCESS FOR PREPARING BENZISOTHIAZOL-3-YL-PEPERAZIN-L-YL-METHYL-CYCLO HEXYL-METHANISOINDOL-1,3-DIONE AND ITS INTERMEDIATES

The present invention discloses process for preparing benzisothiazol-3-yl- piperazin-l-yl-methyl-cyclo hexyl-methanisoindol-l,3-dione and intermediates thereof.

PROCESS FOR THE PREPARATION OF AN ANTIPSYCHOTIC AGENT

The present invention provides a process for the preparation of an antipsychotic agent useful for the treatment of schizophrenia.