Dichloromethane → (E)-3-{[2-(t-Butoxycarbonylamino)-1,3-thiazol-4-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol

HRID 1171722Notes

Reaction equation

[BH4-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[S:12][CH:13]=[C:14](/[CH:16]=[C:17]2\[CH2:18][N:19]([C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][CH2:21][C:22]\2=[O:23])[N:15]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].ClCCl>C(O)C>[C:3]([O:7][C:8]([NH:10][C:11]1[S:12][CH:13]=[C:14](/[CH:16]=[C:17]2\[CH2:18][N:19]([C:24]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:20][CH2:21][CH:22]\2[OH:23])[N:15]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium borohydride (0.27 g) was added to a solution of (E)-3-{[2-(t-butoxycarbonylamino)-1,3-thiazol-4-yl]methylidene}-1-(triphenylmethyl)piperidin-4-one (3.1 g) in a mixed solvent of dichloromethane (15 ml) and ethanol (15 ml), while stirring at 0° C. After being stirred at room temperature for 1.5 hours, the mixture was partitioned between water and ethyl acetate. The organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The extract was concentrated under reduced pressure to afford the title compound as a yellow amorphous solid in a quantitative yield.

Workup

stirringAfter being stirred at room temperature for 1.5 hours
customthe mixture was partitioned between water and ethyl acetate
customThe organic layer was separated
washwashed with a saturated aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
concentrationThe extract was concentrated under reduced pressure

Sources & evidence

ORD record: ord-0cfddc6497c2413d8f2267304c6f7b3c
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829580B2

Reaction notes

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