1H-Pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-, (R)-

Base Information

• Chemical Name: 1H-Pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-, (R)-
• CAS No.: 17958-41-7
• Molecular Formula: C8H13NO
• Mol file: 17958-41-7.mol

Synonyms:

Chemical Property of 1H-Pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-, (R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-, (R)-

There total 18 articles about 1H-Pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-, (R)- 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: 97.0%

5(S)-1-aza-4-(acetoxymethyl)bicyclo<3.3.0>oct-3-en-8-one (122744-13-2) → (-)-supinidine (551-59-7,32430-34-5) + (+)-supinidine (17958-41-7,32430-34-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1.33333h; Yields of byproduct given. Title compound not separated from byproducts; Heating; ee: 78percent;

DOI:10.1016/S0040-4039(00)82286-8

Reference yield: 55.0%

(-)-1-hydroxymethyl-1-phenylseleno-8β-pyrrolizidine (72362-29-9) → (+)-supinidine (17958-41-7,32430-34-5)

Guidance literature:

With dihydrogen peroxide;

DOI:10.1039/P19810000909

Reference yield:

1-(2-Hydroxy-ethyl)-pyrrolidine-2,5-dione (18190-44-8) → (+)-supinidine (17958-41-7,32430-34-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / Et₃N / 4 h / Ambient temperature

2: 65 percent / NaBH₄ / ethanol / 4.5 h / 0 °C

3: 100 percent / 48 h / 30 °C

4: 83 percent / LDA / 1.) -78 deg C, 2 h, 2.) -30 deg C, 3 h; start. mat. is not opt. pure

5: 89 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C / start. mat. is not opt. pure

6: 1.) MCPBA / 1.) CH₂Cl₂, -78 deg C, 30 min. 2.) toluene, reflux, 22 h; start. mat. is not opt. pure

7: Et₃N / DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

8: LiAlH₄ / tetrahydrofuran / 1.33 h / Heating; ee: 78percent

With sodium tetrahydroborate; lithium aluminium tetrahydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; dmap; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)82286-8

upstream raw materials:

5(S)-1-aza-4-(acetoxymethyl)bicyclo<3.3.0>oct-3-en-8-one

(-)-1-hydroxymethyl-1-phenylseleno-8β-pyrrolizidine

(-)-(2S,4R)-N-formyl-4-formyloxyproline

ethyl (+)-6α-hydroxy-8β-pyrrolizidine-1α-carboxylate