4-Toluenesulfonyl chloride → HCID 131734818, compound

HRID 1778501Notes

Reaction equation

[Si:1]([O:8][CH2:9][C:10]1([CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH2:14][CH2:13][CH:12]([CH2:15][OH:16])[N:11]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:33]1([CH3:43])[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Si:26]([O:25][CH2:24][C:10]1([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[CH2:14][CH2:13][CH:12]([CH2:15][O:16][S:39]([C:36]2[CH:37]=[CH:38][C:33]([CH3:43])=[CH:34][CH:35]=2)(=[O:41])=[O:40])[N:11]1[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:27])[CH3:28]

Participants

Conditions

Temperature: 25 °C

Procedure

To a mixture of tert-butyl 2,2-bis[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(hydroxymethyl)pyrrolidine-1-carboxylate (400 mg, 0.82 mmol) and 4-dimethylaminopyridine (300 mg, 2.45 mmol) in DCM (20 mL) was added 4-toluenesulfonyl chloride (312 mg, 1.64 mmol) at 0° C. The mixture was stirred at 25° C. for 16 h. Then the mixture was diluted with DCM (50 mL) and washed with saturated NH4Cl (50 mL) three times, saturated NaHCO3 (50 mL) three times and water (50 mL) three times, dried over anhydrous sodium sulfate and concentrated in vacuo to afford tert-butyl 2,2-bis[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(p-tolylsulfonyloxymethyl)pyrrolidine-1-carboxylate 81i (410 mg, 77%) which was used for next step without further purification. MS: calc'd (MH+) 644, measured (MH+) 644.

Workup

washwashed with saturated NH4Cl (50 mL) three times, saturated NaHCO3 (50 mL) three times and water (50 mL) three times
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5bb61fd58b7f473781ad0f19b8ca6c1b
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266904B2

Reaction notes

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