5-[(1-Tert-butoxycarbonyl-2-propyl-pyrrolidin-2-yl)-hydroxy-methyl]-indole-1-carboxylic acid tert-butyl ester → 5-(1-Tert-butoxycarbonyl-2-propyl-pyrrolidine-2-carbonyl)-indole-1-carboxylic acid tert-butyl ester

HRID 1895036Notes

Reaction equation

HRID 1895036 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]([C:19]3([CH2:31][CH2:32][CH3:33])[CH2:23][CH2:22][CH2:21][N:20]3[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[OH:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([C:19]3([CH2:31][CH2:32][CH3:33])[CH2:23][CH2:22][CH2:21][N:20]3[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 666875405-[(1-Tert-butoxycarbonyl-2-propyl-pyrrolidin-2-yl)-hydroxy-methyl]-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 666873605-(1-Tert-butoxycarbonyl-2-propyl-pyrrolidine-2-carbonyl)-indole-1-carboxylic acid tert-butyl esterYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5-[(1-tert-butoxycarbonyl-2-propyl-pyrrolidin-2-yl)-hydroxy-methyl]-indole-1-carboxylic acid tert-butyl ester (0.460 g, 1.00 mmol) in DCM (10 mL) at 0° C. under nitrogen was added DMP (0.652 g, 1.54 mmol) in a single portion. The reaction mixture warmed to ambient temperature and stirred for 90 minutes, then diluted with DCM, washed with a 1:1 mixture of 10% aqueous Na2S2O5 and NaHCO3, followed by brine, then dried (MgSO4), filtered and concentrated in vacuo to a yellow oil. Purification by chromatography (silica, 0 to 80% EtOAc in hexanes) gave 5-(1-tert-butoxycarbonyl-2-propyl-pyrrolidine-2-carbonyl)-indole-1-carboxylic acid tert-butyl ester (0.132 g, 0.289 mmol, 29%) as a yellow oil.

Workup

  1. washwashed with a 1:1 mixture of 10% aqueous Na2S2O5 and NaHCO3
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a yellow oil
  5. customPurification by chromatography (silica, 0 to 80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e9f092c23d58463cb5d965c0cdcf5f28
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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