Acetone → HCID 90300391, compound

HRID 514626Notes

Reaction equation

[O:1]([CH2:19][C:20]1([CH2:28][N:29]2[CH:33]=[C:32]([CH:34]=[O:35])[N:31]=[C:30]2[N+:36]([O-:38])=[O:37])[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22][CH2:21]1)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+].CC(C)=O>C(O)C>[O:1]([CH2:19][C:20]1([CH2:28][N:29]2[CH:33]=[C:32]([CH2:34][OH:35])[N:31]=[C:30]2[N+:36]([O-:38])=[O:37])[CH2:25][O:24][C:23]([CH3:26])([CH3:27])[O:22][CH2:21]1)[Si:2]([C:15]([CH3:17])([CH3:16])[CH3:18])([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 25 °C

Procedure

107 mg (0.20 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-[(4-formyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane was dissolved in 3.0 mL of ethanol, 10 mg (0.24 mmol equivalents) of sodium borohydride was added thereto, and the mixture was stirred at room temperature (25° C.) for 10 minutes. After completion of the reaction, acetone was added dropwise, and the mixture was concentrated under vacuum. The obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=1/1) to give 101 mg (0.19 mmol equivalents) of 5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-5-{(4-hydroxymethyl-2-nitro-1H-imidazol-1-yl)methyl}-1,3-dioxane.

Workup

additionwas added dropwise
concentrationthe mixture was concentrated under vacuum
customThe obtained crude product
customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=1/1)

Sources & evidence

ORD record: ord-efa4b050e2d047b3a6d07a91fd609a0e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107964B2

Reaction notes

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