Water → HCID 86682811, compound

HRID 1504338Notes

Reaction equation

HRID 1504338 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][O:14][CH3:15])[CH2:10][C@H:9]1[C:16]([OH:18])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=1)=[O:22].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:15][O:14][CH2:13][C@@H:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@H:9]([C:16]([O:18][CH2:20][C:21]([C:23]2[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=2)=[O:22])=[O:17])[CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 74544-Bromophenacyl bromideHCID 8471TriethylamineHCID 696720591,2-Pyrrolidinedicarboxylic acid, 4-(methoxymethyl)-, 1-(1,1-dimethylethyl) ester, (2S,4S)-

Product 1

HCID 86682811HCID 86682811, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-1-(tert-butoxycarbonyl)-4-(methoxymethyl)pyrrolidine-2-carboxylic acid (10 g, 38.61 mmol) in DCM (100 mL) was added (2-bromo-1-(4-bromophenyl)-ethanone (11.8 g, 42.47 mmol) and triethylamine (7.8 g, 77.22 mmol). The reaction mixture was stirred at RT for 3 h. Water was added and the mixture was extracted with EtOAc. The organic phase was dried over sodium sulfate, concentrated, and purified by column chromatography to provide the title intermediate (12 g, 56% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ(ppm) 1.438-1.466 (d, 9H, J=11.2 Hz), 2.024-2.056 (t, 1H, J=12.8 Hz), 2.553 (s, 2H), 3.214-3.776 (m, 6H), 4.410-4.850 (t, 1H, J=15 Hz), 5.155-5.549 (m, 1H), 7.270-7.278 (t, 1H, J=1.6 Hz), 7.636-7.654 (d, 1H, J=7.2 Hz), 7.765-7.774 (d, 1H, J=3.6 Hz).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-98213cac7b65455bbd1e5c805fd8c336
Source dataset
uspto-grants-2015_12
Patent number
US09212168B2

Reaction notes

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