Lithium borohydride → HCID 46917447, compound

HRID 339639Notes

Reaction equation

HRID 339639 reaction equation
[BH4-].[Li+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:15][C:16](=[O:38])[CH:17]=[C:18]2[CH2:23][CH2:22][N:21]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH2:20][CH2:19]2)[C:11](OC)=[O:12])=[CH:6][CH:5]=1>C1COCC1>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:15][C:16](=[O:38])[CH:17]=[C:18]2[CH2:23][CH2:22][N:21]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([O:33][C:34]([F:35])([F:37])[F:36])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH2:20][CH2:19]2)[CH2:11][OH:12])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 46917449HCID 46917449, compound

Product 1

HCID 46917447HCID 46917447, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium borohydride (42.3 mg, 1.94 mmol) in THF (3 ml) was added at 0° C. to a solution of methyl 2-(4-fluorophenyl)-2-(2-(1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-ylidene)acetamido)acetate prepared in EXAMPLE 19 (350 mg, 0.647 mmol) in THF (7 ml) and the whole was stirred at room temperature for 18 hours. The reaction mixture was quenched with H2O and the resulting precipitation was collected and washed with H2O and n-hexane to give N-(1-(4-fluorophenyl)-2-hydroxyethyl)-2-(1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-ylidene)acetamide (298 mg, 92%) as a white solid: LCMS: 503 {M+1}+. 1H NMR (DMSO-d6)□ δ: 2.27 (m, 2H), 2.98-3.06 (m, 6H), 3.51 (m, 2H), 4.84 (m, 2H), 5.78 (s, 1H), 7.10 (m, 2H), 7.29 (m, 2H), 7.61 (d, 2H), 7.89 (d, 2H), 8.29 (d, 1H).

Workup

  1. customThe reaction mixture was quenched with H2O
  2. customthe resulting precipitation
  3. customwas collected
  4. washwashed with H2O and n-hexane

Sources & evidence

ORD record
ord-28cecd605bb34d708b3a1ae03f892039
Source dataset
uspto-grants-2014_11
Patent number
US08895551B2

Reaction notes

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