HCID 131734816, compound → HCID 131734815, compound

HRID 1778499Notes

Reaction equation

[C:1]([O:4][CH2:5][CH:6]1[CH2:10][CH2:9][C:8]([CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[N:7]1CC1C=CC=CC=1)(=[O:3])[CH3:2]>C(O)C.[OH-].[Pd+2].[OH-]>[C:1]([O:4][CH2:5][CH:6]1[CH2:10][CH2:9][C:8]([CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24])([CH2:11][O:12][Si:13]([C:16]([CH3:18])([CH3:19])[CH3:17])([CH3:14])[CH3:15])[NH:7]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

The mixture of [1-benzyl-5,5-bis[[tert-butyl(dimethyl)silyl]oxymethyl]pyrrolidin-2-yl]methyl acetate 81e (5.7 g, 10.94 mmol) and 20% palladium hydroxide on active carbon (1 g) in ethanol (150 mL) was stirred at 50° C. under 2.5 Mpa of H2 pressure for 16 hours. Then the catalyst was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford [5,5-bis[[tert-butyl(dimethyl)silyl]oxymethyl]pyrrolidin-2-yl]methyl acetate 81f (4.48 g, 95%) which was used for next step without further purification. MS: calc'd (MH+) 432, measured (MH+) 432.

Workup

filtrationThen the catalyst was filtered off
washwashed with ethyl acetate
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-236dbd73ccb44f2e8e18dd05dcc88091
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266904B2

Reaction notes

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