2-Pyrrolidinone, 4-(acetyloxy)-1-[2,2-dimethyl-5-(phenylmethoxy)-3-pentenyl]-5-hydroxy-

Base Information

• Chemical Name: 2-Pyrrolidinone, 4-(acetyloxy)-1-[2,2-dimethyl-5-(phenylmethoxy)-3-pentenyl]-5-hydroxy-
• CAS No.: 86545-49-5
• Molecular Formula: C20H27NO5
• Molecular Weight: 361.438
• Mol file: 86545-49-5.mol

Synonyms:

Chemical Property of 2-Pyrrolidinone, 4-(acetyloxy)-1-[2,2-dimethyl-5-(phenylmethoxy)-3-pentenyl]-5-hydroxy-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Pyrrolidinone, 4-(acetyloxy)-1-[2,2-dimethyl-5-(phenylmethoxy)-3-pentenyl]-5-hydroxy-

There total 12 articles about 2-Pyrrolidinone, 4-(acetyloxy)-1-[2,2-dimethyl-5-(phenylmethoxy)-3-pentenyl]-5-hydroxy- 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: 83.0%

(+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione (86534-22-7) → 4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3(E)-en-1yl>-5-hydroxy-2-pyrrolidinone (86545-49-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; at -25 ℃; for 0.333333h;

DOI:10.1021/jo00202a016

Reference yield:

3,3-dimethyl acrylaldehyde (107-86-8) → 4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3(E)-en-1yl>-5-hydroxy-2-pyrrolidinone (86545-49-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) n-BuLi / 1.) THF, hexane, -60 deg C, 10 min, 2.) -65 deg C, 30 min

2: propionic acid / 145 - 180 °C

3: 10percent aq. NaOH / 6 h / Heating

4: 71 percent / thionyl chloride / 1 h / Heating

5: NaN₃ / acetone; H₂O / 0.5 h / 0 °C

6: benzene / 1 h / Heating

7: t-BuOK / 0.5 h / Ambient temperature

8: 86 percent / trifluoroacetic acid (TFA) / 0.5 h / Ambient temperature

9: CH₂Cl₂ / 18 h / Ambient temperature

10: acetyl chloride / CH₂Cl₂ / 30 h / 40 °C

11: 83 percent / NaBH₄ / methanol / 0.33 h / -25 °C

With sodium hydroxide; sodium tetrahydroborate; n-butyllithium; thionyl chloride; sodium azide; potassium tert-butylate; propionic acid; acetyl chloride; trifluoroacetic acid; In methanol; dichloromethane; water; acetone; benzene;

DOI:10.1021/jo00202a016

Reference yield:

6-(benzyloxy)-3,3-dimethyl-4-hexenoyl chloride (86534-20-5) → 4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3(E)-en-1yl>-5-hydroxy-2-pyrrolidinone (86545-49-5)

Guidance literature:

Multi-step reaction with 7 steps

1: NaN₃ / acetone; H₂O / 0.5 h / 0 °C

2: benzene / 1 h / Heating

3: t-BuOK / 0.5 h / Ambient temperature

4: 86 percent / trifluoroacetic acid (TFA) / 0.5 h / Ambient temperature

5: CH₂Cl₂ / 18 h / Ambient temperature

6: acetyl chloride / CH₂Cl₂ / 30 h / 40 °C

7: 83 percent / NaBH₄ / methanol / 0.33 h / -25 °C

With sodium tetrahydroborate; sodium azide; potassium tert-butylate; acetyl chloride; trifluoroacetic acid; In methanol; dichloromethane; water; acetone; benzene;

DOI:10.1021/jo00202a016

upstream raw materials:

(+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione

3,3-dimethyl acrylaldehyde

4-Methyl-1-(phenylmethoxy)-3-penten-2-ol

(E)-6-(benzyloxy)-3,3-dimethyl-4-hexenoic acid

Downstream raw materials:

(+)-1(S)-acetoxy-7(S)-<(benzyloxy)methyl>-6(R)-(2-hydroxyprop-2-yl)-7a(R)-hexahydro-3H-pyrrolizin-3-one

1(S)-acetoxy-6(R)-(2-formyloxyprop-2-yl)-7(S)-<(benzyloxy)methyl>-7a(R)-hexahydro-3H-pyrrolizin-3-one

Acetic acid (1R,7S,7aS)-7-acetoxymethyl-hexahydro-pyrrolizin-1-yl ester

(+)-7(S)-<(benzyloxy)methyl>-1(R)-hydroxy-6(S)-(2-hydroxyprop-2-yl)-7a(R)-hexahydro-3H-pyrrolizin-3-one