(1S,3'S)-<2'-<1'-(2'',4''-dimethoxybenzyl)-2'-oxo-piperidin-3'-yl>-1-hydroxymethylethyl>-carbamic acid tert-butyl ester

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Chemical Name:(1S,3'S)-<2'-<1'-(2'',4''-dimethoxybenzyl)-2'-oxo-piperidin-3'-yl>-1-hydroxymethylethyl>-carbamic acid tert-butyl ester
CAS No.:223526-46-3
Molecular Formula:C₂₂H₃₄N₂O₆
Molecular Weight:422.522
Hs Code.:

Synonyms:(1S,3'S)-<2'-<1'-(2'',4''-dimethoxybenzyl)-2'-oxo-piperidin-3'-yl>-1-hydroxymethylethyl>-carbamic acid tert-butyl ester

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Chemical Property of (1S,3'S)-<2'-<1'-(2'',4''-dimethoxybenzyl)-2'-oxo-piperidin-3'-yl>-1-hydroxymethylethyl>-carbamic acid tert-butyl ester

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Technology Process of (1S,3'S)-<2'-<1'-(2'',4''-dimethoxybenzyl)-2'-oxo-piperidin-3'-yl>-1-hydroxymethylethyl>-carbamic acid tert-butyl ester

There total 7 articles about (1S,3'S)-<2'-<1'-(2'',4''-dimethoxybenzyl)-2'-oxo-piperidin-3'-yl>-1-hydroxymethylethyl>-carbamic acid tert-butyl ester 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:

: 223526-44-1
(S)-4-[(S)-1-(2,4-Dimethoxy-benzyl)-2-oxo-piperidin-3-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 223526-46-3
(1S,3'S)-<2'-<1'-(2'',4''-dimethoxybenzyl)-2'-oxo-piperidin-3'-yl>-1-hydroxymethylethyl>-carbamic acid tert-butyl ester

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 50 ℃; for 2.5h; Yield given;
DOI:10.1021/jm9805384

Reference yield:

: 136904-77-3
(4S)-4-(2-methoxycarbonylethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 223526-46-3
(1S,3'S)-<2'-<1'-(2'',4''-dimethoxybenzyl)-2'-oxo-piperidin-3'-yl>-1-hydroxymethylethyl>-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: aq. 4.0 M NaOH / methanol / 3.5 h / 23 °C

2: 1.) pivaloyl chloride, Et₃N, 2.) LiCl / 1.) THF, 0 deg C, 3.5 h, 2.) THF, 23 deg C, 19 h

3: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 20 min, 2.) THF, a) -78 deg C, 3 h, b) -45 deg C, 2 h

4: 1.) BH₃*THF, 2.) aq. NaBO₃*4H₂O / 1.) THF, 0 deg C, 30 min, 2.) THF, 25 deg C, 1 h

5: 3.53 g / SO₃*pyridine, Et₃N / dimethylsulfoxide / 3 h / 23 °C

6: NaOAc, NaBH₃CN / tetrahydrofuran; ethanol / 20 h / 23 °C

7: p-TsOH*H₂O / methanol / 2.5 h / 50 °C

With sodium perborate; sodium hydroxide; borane-THF; pyridine-SO₃ complex; sodium acetate; sodium hexamethyldisilazane; pivaloyl chloride; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; lithium chloride; In tetrahydrofuran; methanol; ethanol; dimethyl sulfoxide;
DOI:10.1021/jm9805384

Reference yield:

: 223526-25-8
(4S)-4-(2'-carboxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 223526-46-3
(1S,3'S)-<2'-<1'-(2'',4''-dimethoxybenzyl)-2'-oxo-piperidin-3'-yl>-1-hydroxymethylethyl>-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) pivaloyl chloride, Et₃N, 2.) LiCl / 1.) THF, 0 deg C, 3.5 h, 2.) THF, 23 deg C, 19 h

2: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 20 min, 2.) THF, a) -78 deg C, 3 h, b) -45 deg C, 2 h

3: 1.) BH₃*THF, 2.) aq. NaBO₃*4H₂O / 1.) THF, 0 deg C, 30 min, 2.) THF, 25 deg C, 1 h

4: 3.53 g / SO₃*pyridine, Et₃N / dimethylsulfoxide / 3 h / 23 °C

5: NaOAc, NaBH₃CN / tetrahydrofuran; ethanol / 20 h / 23 °C

6: p-TsOH*H₂O / methanol / 2.5 h / 50 °C

With sodium perborate; borane-THF; pyridine-SO₃ complex; sodium acetate; sodium hexamethyldisilazane; pivaloyl chloride; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; lithium chloride; In tetrahydrofuran; methanol; ethanol; dimethyl sulfoxide;
DOI:10.1021/jm9805384