trans-1-(tert-Butoxycarboxyl)-2(S)-(methoxycarbonyl)-5(S)-<(tosyloxy)methyl>pyrrolidine

Base Information

Chemical Name:trans-1-(tert-Butoxycarboxyl)-2(S)-(methoxycarbonyl)-5(S)-<(tosyloxy)methyl>pyrrolidine
CAS No.:120980-88-3
Molecular Formula:C₁₉H₂₇NO₇S
Molecular Weight:413.492
Hs Code.:

Synonyms:trans-1-(tert-Butoxycarboxyl)-2(S)-(methoxycarbonyl)-5(S)-<(tosyloxy)methyl>pyrrolidine

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Chemical Property of trans-1-(tert-Butoxycarboxyl)-2(S)-(methoxycarbonyl)-5(S)-<(tosyloxy)methyl>pyrrolidine

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Technology Process of trans-1-(tert-Butoxycarboxyl)-2(S)-(methoxycarbonyl)-5(S)-<(tosyloxy)methyl>pyrrolidine

There total 9 articles about trans-1-(tert-Butoxycarboxyl)-2(S)-(methoxycarbonyl)-5(S)-<(tosyloxy)methyl>pyrrolidine 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%

: 136175-14-9
(2S-trans)-5-(Hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl diester

: 98-59-9
p-toluenesulfonyl chloride

: 120980-88-3
trans-1-(tert-Butoxycarboxyl)-2(S)-(methoxycarbonyl)-5(S)-<(tosyloxy)methyl>pyrrolidine

Guidance literature:: In pyridine;
DOI:10.1016/S0040-4039(00)80644-9

Reference yield:

: 118396-01-3
(-)-(2S,5S)-N-benzyl-trans-2,5-bis(methoxycarbonyl)pyrrolidine

: 120980-88-3
trans-1-(tert-Butoxycarboxyl)-2(S)-(methoxycarbonyl)-5(S)-<(tosyloxy)methyl>pyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / H₂/Pd / ethanol

2: 90 percent / acetonitrile

3: NaOH / H₂O

4: LiBH₄

6: 83 percent / pyridine

With sodium hydroxide; lithium borohydride; hydrogen; palladium; In pyridine; ethanol; water; acetonitrile;
DOI:10.1016/S0040-4039(00)80644-9

Reference yield:

: 90290-04-3,50990-24-4,17740-40-8,52321-06-9,90365-12-1
trans-N-benzyl-2,5-bis(ethoxycarbonyl)pyrrolidine

: 120980-88-3
trans-1-(tert-Butoxycarboxyl)-2(S)-(methoxycarbonyl)-5(S)-<(tosyloxy)methyl>pyrrolidine

Guidance literature:: Multi-step reaction with 8 steps

1: NaOH / H₂O / 8 h / 23 °C

2: 1) SOCl₂ / 1) 0 deg C, 2) reflux, 4 h

3: 91 percent / H₂ / 10percent P/C / ethanol / 18 h / 40 °C / 2585.7 Torr

4: 90 percent / acetonitrile / 60 h / 23 °C

5: 63 percent / aq. NaOH / methanol / 20 h / 23 °C

6: 1) LiBH₄, 2) H₂O / 1) THF, a) 0 deg C, 1 h, b) 23 deg C, 12 h

7: tetrahydrofuran; diethyl ether

8: pyridine / 18 h / 0 °C

With pyridine; sodium hydroxide; lithium borohydride; thionyl chloride; water; hydrogen; 10percent P/C; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; acetonitrile;
DOI:10.1021/jo00023a037