N-[(1R,2R,6R)-4-bromo-2-(1-ethylpropoxy)-6-hydroxycyclohex-3-en-1-yl]acetamide

Base Information

Chemical Name:N-[(1R,2R,6R)-4-bromo-2-(1-ethylpropoxy)-6-hydroxycyclohex-3-en-1-yl]acetamide
CAS No.:1122581-40-1
Molecular Formula:C₁₃H₂₂BrNO₃
Molecular Weight:320.227
Hs Code.:

Synonyms:N-[(1R,2R,6R)-4-bromo-2-(1-ethylpropoxy)-6-hydroxycyclohex-3-en-1-yl]acetamide

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Chemical Property of N-[(1R,2R,6R)-4-bromo-2-(1-ethylpropoxy)-6-hydroxycyclohex-3-en-1-yl]acetamide

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Technology Process of N-[(1R,2R,6R)-4-bromo-2-(1-ethylpropoxy)-6-hydroxycyclohex-3-en-1-yl]acetamide

There total 4 articles about N-[(1R,2R,6R)-4-bromo-2-(1-ethylpropoxy)-6-hydroxycyclohex-3-en-1-yl]acetamide 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:

: 1062100-77-9
(1S,2R,5R,6S)-6-acetamido-2,3-dibromo-5-(1-ethylpropoxy)-cyclohex-3-en-1-yl acetate

: 1122581-40-1
N-[(1R,2R,6R)-4-bromo-2-(1-ethylpropoxy)-6-hydroxycyclohex-3-en-1-yl]acetamide

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1002/anie.200801959

Reference yield:

: 67451-62-1,82683-92-9,132958-32-8,130792-45-9
cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

: 1122581-40-1
N-[(1R,2R,6R)-4-bromo-2-(1-ethylpropoxy)-6-hydroxycyclohex-3-en-1-yl]acetamide

Guidance literature:: Multi-step reaction with 7 steps

1: acetone / 0.5 h / 0 - 20 °C

2: stannic bromide / acetonitrile; water / 8 h / 0 °C

3: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -10 - 0 °C

4: boron trifluoride diethyl etherate / 6 h / -10 - 0 °C

5: hydrogenchloride / methanol; water / 6 h / 50 °C

6: tetrahydrofuran / 3.5 h / 0 - 25 °C

7: C₆H₁₆B*HLi / tetrahydrofuran / 2 h / 0 - 25 °C

With hydrogenchloride; C₆H₁₆B*HLi; boron trifluoride diethyl etherate; stannic bromide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; water; acetone; acetonitrile;
DOI:10.1021/jm3008486

Reference yield:

: 1106677-14-8
N-[(3aR,4R,5S,7aS)-4,7-dibromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-yl]acetamide

: 1122581-40-1
N-[(1R,2R,6R)-4-bromo-2-(1-ethylpropoxy)-6-hydroxycyclohex-3-en-1-yl]acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -10 - 0 °C

2: boron trifluoride diethyl etherate / 6 h / -10 - 0 °C

3: hydrogenchloride / methanol; water / 6 h / 50 °C

4: tetrahydrofuran / 3.5 h / 0 - 25 °C

5: C₆H₁₆B*HLi / tetrahydrofuran / 2 h / 0 - 25 °C

With hydrogenchloride; C₆H₁₆B*HLi; boron trifluoride diethyl etherate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; water;
DOI:10.1021/jm3008486