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
• Article Data: 12

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

Chemical Properties

White Solid

Uses

(1R,2R)-1,2-Cyclohexanedimethanol (cas# 65376-05-8) is a compound useful in organic synthesis.

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

• 65376-03-6 (3aR,7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran-1-one 
• 1687-29-2 dimethyl cis-1,2-cyclohexanedicarboxylate 
• 88-98-2 trans-cyclohex-4-ene-1,2-dicarboxylic acid 
• 2305-32-0 trans-1,2-cyclohexanedicarboxylic acid 
• 46022-05-3 (1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid 
• 3205-35-4 trans dimethyl cyclohexane-1,2-dicarboxylate 
• 131-11-3 phthalic acid dimethyl ester 
• 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 
• 15753-50-1 cis-1,2-cyclohexanedimethanol 
• 96946-89-3 diethyl trans-1,2,3,6-tetrahydrophthalate 
• 140459-96-7 (1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester 
• 65376-04-7 (-)-(1R,2R)-trans-2-(hydroxymethyl)cyclohexanoic acid 

Downstream Products

• 186204-35-3 (1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate 
• 146611-58-7 ((1R,2R)-2-(((tert-butyldimethylsilyl)oxy)methyl)cyclohexyl)methanol 
• 3205-36-5 (R)-trans-1,2-bis-(toluene-4-sulfonyloxymethyl)-cyclohexane 
• 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 
• 139563-25-0 lurasidone hydrochloride 
• 194861-74-0 lurasidone 

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.

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.

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.