1-Pentyn-3-ol → HCID 86670386, compound

HRID 1972531Notes

Reaction equation

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

Participants

Reactant 2

HCID 929811-Pentyn-3-ol

HCID 86670387HCID 86670387, compound

Product 1

HCID 86670386HCID 86670386, compound

Procedure

Following the procedure described for Example 152, 2-(3-bromo-4-(4-(phenylsulfonyl)piperidin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol was coupled to 1-pentyn-3-ol (Aldrich, St. Louis, Mo.) to afford 1-(5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-(4-(phenylsulfonyl)piperidin-1-yl)phenyl)pent-1-yn-3-ol as a light yellow solid and a mixture of enantiomers.

Sources & evidence

ORD record: ord-a978ddd258d54a05ad86d18d0f802200
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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