Acetonitrile → Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-[2-(3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]ester

HRID 71994Notes

Reaction equation

HRID 71994 reaction equation
Br[CH2:2][C:3]([C:5]1[S:9][CH:8]2[CH:10]=[CH:11][S:12][CH:7]2[CH:6]=1)=[O:4].[C:13]([N:20]1[CH2:27][CH2:26][CH2:25][C@H:21]1[C:22]([OH:24])=[O:23])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].CC#N>C(N(CC)CC)C>[S:9]1[C:5]([C:3](=[O:4])[CH2:2][O:24][C:22]([CH:21]2[CH2:25][CH2:26][CH2:27][N:20]2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:23])=[CH:6][CH:7]2[S:12][CH:11]=[CH:10][CH:8]12

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 58545558HCID 58545558, compound

Product 1

HCID 66620078Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-[2-(3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]esterYield 61%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Crude 2-Bromo-1-(3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-ethanone (2.48 mmol assuming complete conversion from starting material) was treated with Boc-proline and MeCN (25 mL). Triethylamine was added and the solution was stirred at RT for 1 h then concentrated. The crude residue was purified by silica column chromatography (14% to 35% EtOAc/Hex) to afford the title compound (595 mg, 61%).

Workup

  1. concentrationthen concentrated
  2. customThe crude residue was purified by silica column chromatography (14% to 35% EtOAc/Hex)

Sources & evidence

ORD record
ord-bec1896fd7ad48a28e99653db7d86ac8
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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