1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl(3aR,4S,6aS)-2-(3-methyl-2-phenylbutanoyl)octahydrocyclopenta[c]pyrrol-4-ylcarbamate

HRID 1092562Notes

Reaction equation

HRID 1092562 reaction equation
[CH3:1][CH:2]([CH3:13])[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[CH2:35]1[C@H:39]2[CH2:40][CH2:41][C@H:42]([NH:43][C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[C@H:38]2[CH2:37][NH:36]1>ClCCl>[CH3:13][CH:2]([CH3:1])[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([N:36]1[CH2:37][C@@H:38]2[C@@H:42]([NH:43][C:44](=[O:50])[O:45][C:46]([CH3:48])([CH3:47])[CH3:49])[CH2:41][CH2:40][C@@H:39]2[CH2:35]1)=[O:6]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 190243-Methyl-2-phenylbutanoic acidHCID 757711-HydroxybenzotriazoleHCID 51723436tert-Butyl ((1S,5R,6S)-3-azabicyclo[3.3.0]octan-6-yl)carbamate

Product 1

HCID 66590911tert-butyl(3aR,4S,6aS)-2-(3-methyl-2-phenylbutanoyl)octahydrocyclopenta[c]pyrrol-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methyl-2-phenylbutanoic acid (63 mg, 0.353 mmol), 1-hydroxybenzotriazole (54.1 mg, 0.353 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.063 mL, 0.353 mmol) were combined in dichloromethane (5 mL). The reaction was stirred at room temperature for 20 minutes, and then tert-butyl(3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-ylcarbamate (80 mg, 0.353 mmol) from Step B was added. After 30 minutes, the reaction was quenched with water and extracted with dichloromethane. The combined extracts were concentrated, and the crude material purified using 10-100% ethyl acetate/hexanes to give tert-butyl(3aR,4S,6aS)-2-(3-methyl-2-phenylbutanoyl)octahydrocyclopenta[c]pyrrol-4-ylcarbamate: MS (ESI+) m/z 387 (M+H)+.

Workup

  1. waitAfter 30 minutes
  2. customthe reaction was quenched with water
  3. extractionextracted with dichloromethane
  4. concentrationThe combined extracts were concentrated
  5. customthe crude material purified

Sources & evidence

ORD record
ord-0bdfbda019ca45d69c6799e55fc3b9a6
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

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