tert-butyl (1S,2S,3R,5S)-2,6,6-trimethyl-3-{[(R)-1-phenylethyl]carbamoyl}bicyclo[3.1.1]heptan-2-ylcarbamate

Base Information

Chemical Name:tert-butyl (1S,2S,3R,5S)-2,6,6-trimethyl-3-{[(R)-1-phenylethyl]carbamoyl}bicyclo[3.1.1]heptan-2-ylcarbamate
CAS No.:1474047-41-0
Molecular Formula:C₂₄H₃₆N₂O₃
Molecular Weight:400.561
Hs Code.:

Synonyms:tert-butyl (1S,2S,3R,5S)-2,6,6-trimethyl-3-{[(R)-1-phenylethyl]carbamoyl}bicyclo[3.1.1]heptan-2-ylcarbamate

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Chemical Property of tert-butyl (1S,2S,3R,5S)-2,6,6-trimethyl-3-{[(R)-1-phenylethyl]carbamoyl}bicyclo[3.1.1]heptan-2-ylcarbamate

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Technology Process of tert-butyl (1S,2S,3R,5S)-2,6,6-trimethyl-3-{[(R)-1-phenylethyl]carbamoyl}bicyclo[3.1.1]heptan-2-ylcarbamate

There total 4 articles about tert-butyl (1S,2S,3R,5S)-2,6,6-trimethyl-3-{[(R)-1-phenylethyl]carbamoyl}bicyclo[3.1.1]heptan-2-ylcarbamate 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: 70.0%

: 705949-07-1
C₁₆H₂₇NO₄

: 3886-69-9
(R)-1-phenyl-ethyl-amine

: 1474047-41-0
tert-butyl (1S,2S,3R,5S)-2,6,6-trimethyl-3-{[(R)-1-phenylethyl]carbamoyl}bicyclo[3.1.1]heptan-2-ylcarbamate

Guidance literature:: C₁₆H₂₇NO₄; With triethylamine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; at -10 ℃; for 1h; Inert atmosphere;

(R)-1-phenyl-ethyl-amine; With 4-methyl-morpholine; In tetrahydrofuran; dichloromethane; at -10 - 20 ℃; for 20h; Inert atmosphere;
DOI:10.1055/s-0033-1339291

Reference yield:

: 7785-70-8,25766-18-1
(+)-α-pinene

: 1474047-41-0
tert-butyl (1S,2S,3R,5S)-2,6,6-trimethyl-3-{[(R)-1-phenylethyl]carbamoyl}bicyclo[3.1.1]heptan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium sulfite / 2 h

2.1: dmap / acetonitrile / 12 h / 20 °C

3.1: lithium hydroxide; water / tetrahydrofuran / 12 h / 20 °C

4.1: triethylamine; isobutyl chloroformate / tetrahydrofuran; dichloromethane / 1 h / -10 °C / Inert atmosphere

4.2: 20 h / -10 - 20 °C / Inert atmosphere

With dmap; water; triethylamine; lithium hydroxide; sodium sulfite; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1055/s-0033-1339291

Reference yield:

: 35182-62-8,328010-05-5
(1S,2S,5R,7S)-2,8,8-trimethyl-3-azatricyclo[5.1.1.0^2,5]nonan-4-one

: 1474047-41-0
tert-butyl (1S,2S,3R,5S)-2,6,6-trimethyl-3-{[(R)-1-phenylethyl]carbamoyl}bicyclo[3.1.1]heptan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: dmap / acetonitrile / 12 h / 20 °C

2.1: lithium hydroxide; water / tetrahydrofuran / 12 h / 20 °C

3.1: triethylamine; isobutyl chloroformate / tetrahydrofuran; dichloromethane / 1 h / -10 °C / Inert atmosphere

3.2: 20 h / -10 - 20 °C / Inert atmosphere

With dmap; water; triethylamine; lithium hydroxide; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1055/s-0033-1339291