Triethylamine → HCID 58010887, compound

HRID 2079417Notes

Reaction equation

HRID 2079417 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.C(N(CC)CC)C.Cl[C:22]([O:24][C@H:25]1[CH2:29][CH2:28][O:27][CH2:26]1)=[O:23]>C(Cl)Cl>[C:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][C@@H:2]([NH:1][C:22](=[O:23])[O:24][C@H:25]2[CH2:29][CH2:28][O:27][CH2:26]2)[CH2:3]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidineHCID 22876378(3S)-oxolan-3-yl carbonochloridate

Product 1

HCID 58010887HCID 58010887, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 3-aminopyrrolidine-1-carboxylate (500 mg, 2.6 mmol) in 5 mL CH2Cl2 was added triethylamine (0.73 mL, 5.2 mmol), and the reaction was cooled to −20° C. (S)-tetrahydrofuran-3-yl chloroformate (525 mg, 3.48 mmol) was added in portions over a period of 10 minutes to the above reaction mixture. After allowing the reaction to warm to room temperature, it was quenched with water and extracted twice with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to afford (S)-tetrahydrofuran-3-yl (R)-1-(tert-butoxycarbonyl)pyrrolidin-3-ylcarbamate. Purification via silica gel chromatography using 0-20% EtOAc in CH2Cl2 gave (S)-tetrahydrofuran-3-yl (R)-1-(tert-butoxycarbonyl)pyrrolidin-3-ylcarbamate (490 mg, 63%). LC/MS: m/z 301.3 (M+H)+ at 2.35 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. additionwas added in portions over a period of 10 minutes to the above reaction mixture
  2. customthe reaction
  3. customit was quenched with water
  4. extractionextracted twice with CH2Cl2
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8c73348e40f44298b7e09b11d85caf7e
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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