Sodium Carbonate → HCID 68052017, compound

HRID 1428250Notes

Reaction equation

HRID 1428250 reaction equation
[N:1]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:9]2[CH:4]([NH:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C1COCC1>[N:1]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:9]2[CH:4]([N:5]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:6][CH2:7][CH2:8]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 66823462tert-Butyl octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate

Product 1

HCID 68052017HCID 68052017, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The product of Step 4 (HOAc salt; 3.49 g, 12.2 mmol) was added to a flask, followed by THF (55 mL). Aqueous sodium carbonate (2M; 30.5 mL, 60.9 mmol) was added, and the resulting biphasic mixture was cooled to 0° C. Benzyl chloroformate (2.61 mL, 18.3 mmol) was added and the reaction mixture was allowed to stir while the bath naturally warmed to ambient temperature. After 30 minutes the reaction mixture was partitioned between EtOAc and water (100 mL each) and the layers were separated. The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo to a crude oil that was purified by column chromatography on silica gel eluting with EtOAc/hexane (5-30%) (TLC was visualized with CAM staining) to afford the title product as a colorless oil. LRMS calc'd for C20H28N2O4Na [M+Na]+, 383; found 383. 1H NMR (500 MHz, CDCl3) δ 7.39-7.30 (br m, 5H), 5.15 (br s, 2H), 4.70-4.45 (br m, 1H), 4.15-3.95 (br m, 1H), 3.82-3.62 (br d, 1H), 3.50-3.21 (br m, 2H), 2.79 (br pentet, 1H), 2.30-1.90 (br m, 3H), 1.72-1.58 (br m, 1H), 1.45 (s, 9H), 1.40 (br m, 1H), 1.28-1.14 (br m, 1H).

Workup

  1. temperaturenaturally warmed to ambient temperature
  2. customAfter 30 minutes the reaction mixture was partitioned between EtOAc and water (100 mL each)
  3. customthe layers were separated
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a crude oil that
  7. customwas purified by column chromatography on silica gel eluting with EtOAc/hexane (5-30%) (TLC was visualized with CAM staining)

Sources & evidence

ORD record
ord-69fe654396a945f99cd285d32e27ffd4
Source dataset
uspto-grants-2015_01
Patent number
US08937077B2

Reaction notes

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