2-Butyl-2-{[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-phenyl]-hydroxy-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester → 2-Butyl-2-[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-benzoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 661543Notes

Reaction equation

HRID 661543 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]([C:15]1[CH:20]=[CH:19][C:18]([N:21]([Si:26]([CH3:29])([CH3:28])[CH3:27])[Si:22]([CH3:25])([CH3:24])[CH3:23])=[C:17]([Cl:30])[CH:16]=1)[OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:31][CH2:32][CH2:33][CH3:34])[C:13](=[O:14])[C:15]1[CH:20]=[CH:19][C:18]([N:21]([Si:26]([CH3:27])([CH3:29])[CH3:28])[Si:22]([CH3:25])([CH3:24])[CH3:23])=[C:17]([Cl:30])[CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 666875552-Butyl-2-{[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-phenyl]-hydroxy-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 666875712-Butyl-2-[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-benzoyl]-pyrrolidine-1-carboxylic acid tert-butyl esterYield 58.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-butyl-2-{[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-phenyl]-hydroxy-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (0.357 g, 0.678 mmol) in DCM (10 mL) at ambient temperature under nitrogen was added DMP (0.575 g, 1.36 mmol) in a single portion. After one hour the reaction mixture was diluted with DCM, washed with 1 N NaOH and brine, then dried (MgSO4), filtered and concentrated in vacuo to a brown residue (0.290 g). Purification by chromatography (silica, 10% EtOAc in hexanes) gave 2-butyl-2-[3-chloro-4-(1,1,1,3,3,3-hexamethyl-disilazan-2-yl)-benzoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.208 g, 0.397 mmol, 58%) as a clear colourless residue.

Workup

  1. washwashed with 1 N NaOH and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a brown residue (0.290 g)
  5. customPurification by chromatography (silica, 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9d5acbcfdf744dfc8ecba491b128768d
Source dataset
uspto-grants-2011_12
Patent number
US08084623B2

Reaction notes

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