Ethanol → HCID 86585789, compound

HRID 2415749Notes

Reaction equation

HRID 2415749 reaction equation
[BH4-].[Na+].CC1C=[C:6]([C:21](=O)[CH:22]([N:24]2[CH2:29][CH2:28][C:27]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)([OH:30])[CH2:26][CH2:25]2)C)C=CC=1O[Si](C(C)C)(C(C)C)C(C)C.C([OH:41])C>>[F:37][C:34]1[CH:35]=[CH:36][C:31]([C:27]2([OH:30])[CH2:28][CH2:29][N:24]([CH:22]([OH:41])[CH2:21][CH3:6])[CH2:25][CH2:26]2)=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 4311764Sodium borohydrideHCID 22225731HCID 22225731, compound

Product 1

HCID 86585789HCID 86585789, compound

Procedure

A mixture of sodium borohydride (0.564 g, 14.92 mmol) and ethanol (60 mL) was stirred 10 minutes and then 1-(3-methyl-4-triisopropylsilyloxyphenyl)-2-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-propan-1-one (7.66 g, 14.92 mmol in 10 mL of ethanol) was added with two 30 mL ethanol rinses. The reaction mixture was stirred at ambient temperature overnight. The white solid that precipitated was collected by filtration and dried to yield 5.72 g (74%) of (1R*, 2R*)-1-(3-methyl-4-triisopropylsilyloxyphenyl)-2-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl-propan-1-ol, which was suitable for use without further purification and had: m.p. 188-189° C.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature overnight
  2. customThe white solid that precipitated
  3. filtrationwas collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-99f015dc57704cd0a4195ba613d44ce8
Source dataset
uspto-grants-2004_11
Patent number
US06821985B2

Reaction notes

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