3-(4-{(S)-1-[(R)-1-(4-Methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-2-yl)-indole-1-carboxylic acid tert-butyl ester → 3-((S)-4-pyrrolidin-2-yl-pyridine-2-yl)-1H-indole

HRID 1667625Notes

Reaction equation

HRID 1667625 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[CH:22]=[C:21]([C@@H:23]3[CH2:27][CH2:26][CH2:25][N:24]3[C@@H](C3C=CC(OC)=CC=3)C)[CH:20]=[CH:19][N:18]=2)=[CH:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[NH:24]1[CH2:25][CH2:26][CH2:27][C@H:23]1[C:21]1[CH:20]=[CH:19][N:18]=[C:17]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8][CH:9]=2)[CH:22]=1

Participants

3

Reactant 1

HCID 668898973-(4-{(S)-1-[(R)-1-(4-Methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-2-yl)-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 668898983-((S)-4-pyrrolidin-2-yl-pyridine-2-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-(4-{(S)-1-[(R)-1-(4-Methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-2-yl)-indole-1-carboxylic acid tert-butyl ester (160 mg, 0.31 mmol) in TFA (5 mL) is heated in microwave at 100° C. for 30 min and concentrated down to give crude 3-((S)-4-pyrrolidin-2-yl-pyridine-2-yl)-1H-indole (15), which is used in next step without further purification.

Workup

  1. concentrationconcentrated down

Sources & evidence

ORD record
ord-bf9de904faec4a5ab80eede0c6c06948
Source dataset
uspto-grants-2011_10
Patent number
US08044209B2

Reaction notes

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