(6R^*,7S^*,8S^*)-7-butyl-8-(4-methylphenylsulfonyloxy)-1-azaspiro<5.5>undecan-2-one

Base Information

• Chemical Name: (6R^*,7S^*,8S^*)-7-butyl-8-(4-methylphenylsulfonyloxy)-1-azaspiro<5.5>undecan-2-one
• CAS No.: 80090-62-6
• Molecular Formula: C₂₁H₃₁NO₄S
• Molecular Weight: 393.547
• Mol file: 80090-62-6.mol

Synonyms:

Chemical Property of (6R^*,7S^*,8S^*)-7-butyl-8-(4-methylphenylsulfonyloxy)-1-azaspiro<5.5>undecan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R^*,7S^*,8S^*)-7-butyl-8-(4-methylphenylsulfonyloxy)-1-azaspiro<5.5>undecan-2-one

There total 29 articles about (6R^*,7S^*,8S^*)-7-butyl-8-(4-methylphenylsulfonyloxy)-1-azaspiro<5.5>undecan-2-one 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:

methyl (1R*,2S*,3S*)-2-butyl-3-hydroxy-1-cyclohexanecarboxylate (80090-54-6,84277-34-9,88823-65-8,88823-68-1,90411-07-7) → (6R*,7S*,8S*)-7-butyl-8-(4-methylphenylsulfonyloxy)-1-azaspiro<5.5>undecan-2-one (80090-62-6,84277-45-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / pyridinium p-toluenesulfonate / CHCl₃ / 2 h / 0 °C

3: 92 percent / pyridinium p-toluenesulfonate / CHCl₃ / 1 h / 0 °C

4: 1.) N-methylmorpholine N-oxide, osmium tetroxide, 2.) sodium periodate / 1.) THF/water, RT, 15 min, 2.) THF/water, RT, 3.5 h

5: 1.) NaH / diethyl ether / 0 °C / 1.) 0 deg C, 1 h, 2.) 0 deg C, 15 min

6: 98 percent / H₂ / PtO_2.2H₂O / ethanol

7: 87 percent / KH / tetrahydrofuran / 2.5 h / -5 °C

8: 92 percent / LiCl, NaHCO₃ / dimethylsulfoxide; H₂O / 3 h / 150 °C

9: 87 percent / hydroxylamine hydrochloride, sodium acetate / methanol; H₂O / 36 h / 170 °C / sealed tube

10: 38 percent / pyridine / 20 h / 0 °C

With pyridine; sodium periodate; osmium(VIII) oxide; hydroxylamine hydrochloride; hydrogen; sodium acetate; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; lithium chloride; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; chloroform; water; dimethyl sulfoxide;

DOI:10.1248/cpb.30.2840

Reference yield:

(1R*,2S*,3S*)-2-butyl-3-tert-butyldimethylsiloxy-1-cyclohexanecarboxylic acid → (6R*,7S*,8S*)-7-butyl-8-(4-methylphenylsulfonyloxy)-1-azaspiro<5.5>undecan-2-one (80090-62-6,84277-45-2)

Guidance literature:

Multi-step reaction with 12 steps

1: diethyl ether

2: 97 percent / 5percent aq. HCl / methanol; tetrahydrofuran / 4 h / Ambient temperature

3: 95 percent / pyridinium p-toluenesulfonate / CHCl₃ / 2 h / 0 °C

5: 92 percent / pyridinium p-toluenesulfonate / CHCl₃ / 1 h / 0 °C

6: 1.) N-methylmorpholine N-oxide, osmium tetroxide, 2.) sodium periodate / 1.) THF/water, RT, 15 min, 2.) THF/water, RT, 3.5 h

7: 1.) NaH / diethyl ether / 0 °C / 1.) 0 deg C, 1 h, 2.) 0 deg C, 15 min

8: 98 percent / H₂ / PtO_2.2H₂O / ethanol

9: 87 percent / KH / tetrahydrofuran / 2.5 h / -5 °C

10: 92 percent / LiCl, NaHCO₃ / dimethylsulfoxide; H₂O / 3 h / 150 °C

11: 87 percent / hydroxylamine hydrochloride, sodium acetate / methanol; H₂O / 36 h / 170 °C / sealed tube

12: 38 percent / pyridine / 20 h / 0 °C

With pyridine; hydrogenchloride; sodium periodate; osmium(VIII) oxide; hydroxylamine hydrochloride; hydrogen; sodium acetate; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; lithium chloride; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; chloroform; water; dimethyl sulfoxide;

DOI:10.1248/cpb.30.2840

Reference yield:

methyl (1R*,2S*,3S*)-2-butyl-3-hydroxy-1-(2-propenyl)-1-cyclohexanecarboxylate (80090-56-8,84277-36-1) → (6R*,7S*,8S*)-7-butyl-8-(4-methylphenylsulfonyloxy)-1-azaspiro<5.5>undecan-2-one (80090-62-6,84277-45-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / pyridinium p-toluenesulfonate / CHCl₃ / 1 h / 0 °C

2: 1.) N-methylmorpholine N-oxide, osmium tetroxide, 2.) sodium periodate / 1.) THF/water, RT, 15 min, 2.) THF/water, RT, 3.5 h

3: 1.) NaH / diethyl ether / 0 °C / 1.) 0 deg C, 1 h, 2.) 0 deg C, 15 min

4: 98 percent / H₂ / PtO_2.2H₂O / ethanol

5: 87 percent / KH / tetrahydrofuran / 2.5 h / -5 °C

6: 92 percent / LiCl, NaHCO₃ / dimethylsulfoxide; H₂O / 3 h / 150 °C

7: 87 percent / hydroxylamine hydrochloride, sodium acetate / methanol; H₂O / 36 h / 170 °C / sealed tube

8: 38 percent / pyridine / 20 h / 0 °C

With pyridine; sodium periodate; osmium(VIII) oxide; hydroxylamine hydrochloride; hydrogen; sodium acetate; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; lithium chloride; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; chloroform; water; dimethyl sulfoxide;

DOI:10.1248/cpb.30.2840

upstream raw materials:

1-<3-(tert-butyldimethylsiloxy)cyclohex-1-enyl>ethanone

1-[(1S,2R,3R)-2-Butyl-3-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-ethanone

(1R,2S,3S)-2-Butyl-3-hydroxy-cyclohexanecarboxylic acid methyl ester

(1S,2R,3R)-2-Butyl-3-(tetrahydro-furan-2-yloxy)-cyclohexanecarboxylic acid methyl ester