(1R,2S,6R)-2-{[((R)-2-Hydroxymethyl-3,3-dimethyl-butyl)-methyl-amino]-methyl}-6-(3-hydroxy-propoxymethoxymethyl)-4,4-dimethyl-cyclohexanol

Base Information

• Chemical Name: (1R,2S,6R)-2-{[((R)-2-Hydroxymethyl-3,3-dimethyl-butyl)-methyl-amino]-methyl}-6-(3-hydroxy-propoxymethoxymethyl)-4,4-dimethyl-cyclohexanol
• CAS No.: 205943-30-2
• Molecular Formula: C₂₂H₄₅NO₅
• Molecular Weight: 403.603
• Mol file: 205943-30-2.mol

Synonyms:(1R,2S,6R)-2-{[((R)-2-Hydroxymethyl-3,3-dimethyl-butyl)-methyl-amino]-methyl}-6-(3-hydroxy-propoxymethoxymethyl)-4,4-dimethyl-cyclohexanol

Chemical Property of (1R,2S,6R)-2-{[((R)-2-Hydroxymethyl-3,3-dimethyl-butyl)-methyl-amino]-methyl}-6-(3-hydroxy-propoxymethoxymethyl)-4,4-dimethyl-cyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,6R)-2-{[((R)-2-Hydroxymethyl-3,3-dimethyl-butyl)-methyl-amino]-methyl}-6-(3-hydroxy-propoxymethoxymethyl)-4,4-dimethyl-cyclohexanol

There total 13 articles about (1R,2S,6R)-2-{[((R)-2-Hydroxymethyl-3,3-dimethyl-butyl)-methyl-amino]-methyl}-6-(3-hydroxy-propoxymethoxymethyl)-4,4-dimethyl-cyclohexanol 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: 93.0%

(1R,2R,6S)-2-(3-Benzyloxy-propoxymethoxymethyl)-6-{[((R)-2-hydroxymethyl-3,3-dimethyl-butyl)-methyl-amino]-methyl}-4,4-dimethyl-cyclohexanol (205943-45-9) → (1R,2S,6R)-2-{[((R)-2-Hydroxymethyl-3,3-dimethyl-butyl)-methyl-amino]-methyl}-6-(3-hydroxy-propoxymethoxymethyl)-4,4-dimethyl-cyclohexanol (205943-30-2)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran; at -33 ℃; for 4h;

DOI:10.1021/jo971935+

Reference yield:

methyl 5,5-dimethyl-2-oxo-cyclohexanecarboxylate (50388-51-7) → (1R,2S,6R)-2-{[((R)-2-Hydroxymethyl-3,3-dimethyl-butyl)-methyl-amino]-methyl}-6-(3-hydroxy-propoxymethoxymethyl)-4,4-dimethyl-cyclohexanol (205943-30-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) lithium diisopropylamide / 1.) THF, hexanes, 0 deg C, 20 min, 2.) THF, hexanes, room temperature, overnight

2: cerium(III) chloride heptahydrate, sodium borohydride / methanol

3: 99 percent / imidazole / dimethylformamide / Ambient temperature

4: 100 percent / diisobutylaluminum hydride / toluene / 2 h / -78 °C

5: 93 percent / triethylamine, sulfur trioxide-pyridine complex / dimethylsulfoxide; CH₂Cl₂ / 1.5 h / Ambient temperature

6: 1.) titanium(IV) isopropoxide, 2.) sodium cyanoborohydride / 1.) room temperature, 2 h, 2.) ethanol, 20 h

7: 19.3 mg / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

8: 78 percent / triethylamine, 4-(dimethylamino)pyridine / dimethylformamide / 20 h / Ambient temperature

9: 100 percent / lithium, liq. ammonia / tetrahydrofuran / 4 h / -33 °C

10: 1.) n-butyllithium / 1.) THF, hexanes, -78 -> -30 deg C, 2.) THF, hexanes, -78 deg C -> room temperature, overnight

11: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / Ambient temperature

12: 93 percent / lithium, liq. ammonia / tetrahydrofuran / 4 h / -33 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; tetrabutyl ammonium fluoride; ammonia; sulfur trioxide pyridine complex; lithium; diisobutylaluminium hydride; sodium cyanoborohydride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo971935+

Reference yield:

4,4-dimethylcyclohexane-1-one (4255-62-3) → (1R,2S,6R)-2-{[((R)-2-Hydroxymethyl-3,3-dimethyl-butyl)-methyl-amino]-methyl}-6-(3-hydroxy-propoxymethoxymethyl)-4,4-dimethyl-cyclohexanol (205943-30-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 95 percent / sodium hydride / tetrahydrofuran / 2 h / Heating

2: 1.) lithium diisopropylamide / 1.) THF, hexanes, 0 deg C, 20 min, 2.) THF, hexanes, room temperature, overnight

3: cerium(III) chloride heptahydrate, sodium borohydride / methanol

4: 99 percent / imidazole / dimethylformamide / Ambient temperature

5: 100 percent / diisobutylaluminum hydride / toluene / 2 h / -78 °C

6: 93 percent / triethylamine, sulfur trioxide-pyridine complex / dimethylsulfoxide; CH₂Cl₂ / 1.5 h / Ambient temperature

7: 1.) titanium(IV) isopropoxide, 2.) sodium cyanoborohydride / 1.) room temperature, 2 h, 2.) ethanol, 20 h

8: 19.3 mg / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

9: 78 percent / triethylamine, 4-(dimethylamino)pyridine / dimethylformamide / 20 h / Ambient temperature

10: 100 percent / lithium, liq. ammonia / tetrahydrofuran / 4 h / -33 °C

11: 1.) n-butyllithium / 1.) THF, hexanes, -78 -> -30 deg C, 2.) THF, hexanes, -78 deg C -> room temperature, overnight

12: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / Ambient temperature

13: 93 percent / lithium, liq. ammonia / tetrahydrofuran / 4 h / -33 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; tetrabutyl ammonium fluoride; ammonia; sulfur trioxide pyridine complex; lithium; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo971935+

upstream raw materials:

(1R,2R,6S)-2-(3-Benzyloxy-propoxymethoxymethyl)-6-{[((R)-2-hydroxymethyl-3,3-dimethyl-butyl)-methyl-amino]-methyl}-4,4-dimethyl-cyclohexanol

methyl 5,5-dimethyl-2-oxo-cyclohexanecarboxylate

4,4-dimethylcyclohexane-1-one

(1R,2S,6R)-2-({[(R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3,3-dimethyl-butyl]-methyl-amino}-methyl)-6-hydroxymethyl-4,4-dimethyl-cyclohexanol

Downstream raw materials:

1H-imidazole