((2S,3S,3aS,6S,8aR,9S,9aR)-2-Benzyloxymethyl-3,6-dimethyl-dodecahydro-4a-aza-cyclopenta[b]naphthalen-9-yl)-methanol

Base Information

Chemical Name:((2S,3S,3aS,6S,8aR,9S,9aR)-2-Benzyloxymethyl-3,6-dimethyl-dodecahydro-4a-aza-cyclopenta[b]naphthalen-9-yl)-methanol
CAS No.:164229-03-2
Molecular Formula:C₂₃H₃₅NO₂
Molecular Weight:357.536
Hs Code.:

Synonyms:((2S,3S,3aS,6S,8aR,9S,9aR)-2-Benzyloxymethyl-3,6-dimethyl-dodecahydro-4a-aza-cyclopenta[b]naphthalen-9-yl)-methanol

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Chemical Property of ((2S,3S,3aS,6S,8aR,9S,9aR)-2-Benzyloxymethyl-3,6-dimethyl-dodecahydro-4a-aza-cyclopenta[b]naphthalen-9-yl)-methanol

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Technology Process of ((2S,3S,3aS,6S,8aR,9S,9aR)-2-Benzyloxymethyl-3,6-dimethyl-dodecahydro-4a-aza-cyclopenta[b]naphthalen-9-yl)-methanol

There total 19 articles about ((2S,3S,3aS,6S,8aR,9S,9aR)-2-Benzyloxymethyl-3,6-dimethyl-dodecahydro-4a-aza-cyclopenta[b]naphthalen-9-yl)-methanol 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:

: 164228-95-9
(2S,3S,3aS,6S,8aR,9S,9aR)-2-Benzyloxymethyl-3,6-dimethyl-dodecahydro-4a-aza-cyclopenta[b]naphthalene-9-carboxylic acid ethyl ester

: 164229-03-2
((2S,3S,3aS,6S,8aR,9S,9aR)-2-Benzyloxymethyl-3,6-dimethyl-dodecahydro-4a-aza-cyclopenta[b]naphthalen-9-yl)-methanol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 50 ℃; for 3h;
DOI:10.1021/ja00126a015

Reference yield:

: 135191-38-7
methyl (S)-3-hydroxy-7-methyl-6-octenoate

: 164229-03-2
((2S,3S,3aS,6S,8aR,9S,9aR)-2-Benzyloxymethyl-3,6-dimethyl-dodecahydro-4a-aza-cyclopenta[b]naphthalen-9-yl)-methanol

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) BuLi, (iPr)2NH / 1.) THF, hexane, from -50 to -30 deg C, 2.) THF, hexane, HMPA, from -30 deg C to RT, 4 h

2: LiAlH₄ / tetrahydrofuran / 10 h / Heating

3: p-TsOH*H₂O / 0.5 h

4: 1.) O₃, 2.) Ph₃P, 3.) aq. NaHCO₃, Br₂

5: 93 percent / NaH, MeOH / 1,2-dimethoxy-ethane / 13 h / Heating

6: DBU, p-nitrobenzenesulfonylazide / CH₂Cl₂ / 0.5 h / 0 - 25 °C

7: 89 percent / Rh(octanoate)4 / CH₂Cl₂ / 0.08 h

8: LiAlH₄ / tetrahydrofuran / 10 h / Heating

9: 1.) NaH, 2.) Bu₄NI / 1.) THF, RT, 20 min, 2.) THF, RT, 10 h

10: 96 percent / p-TsOH*H₂O / methanol / 0.33 h / Ambient temperature

11: pyridine / CH₂Cl₂ / 18 h / Ambient temperature

12: 56 percent / Bu₄NI, K₂CO₃ / toluene / 3 h / Heating

13: LiHMDS / tetrahydrofuran / 2 h / -78 - 20 °C

14: LiAlH₄ / tetrahydrofuran / 3 h / 50 °C

With pyridine; methanol; p-nitrobenzenesulfonyl azide; lithium aluminium tetrahydride; n-butyllithium; rhodium (II) octanoate dimer; bromine; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; toluene;
DOI:10.1021/ja00126a015

Reference yield:

: 98-09-9
benzenesulfonyl chloride

: 164229-03-2
((2S,3S,3aS,6S,8aR,9S,9aR)-2-Benzyloxymethyl-3,6-dimethyl-dodecahydro-4a-aza-cyclopenta[b]naphthalen-9-yl)-methanol

Guidance literature:: Multi-step reaction with 2 steps

1: LiHMDS / tetrahydrofuran / 2 h / -78 - 20 °C

2: LiAlH₄ / tetrahydrofuran / 3 h / 50 °C

With lithium aluminium tetrahydride; lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1021/ja00126a015