Lithium Chloride → HCID 57659753, compound

HRID 1011595Notes

Reaction equation

HRID 1011595 reaction equation
[Cl-].[Li+].[BH4-].[Na+].[Si:5]([O:12][C@H:13]1[CH2:17][N:16]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C@H:15]([C:31](OC)=[O:32])[CH2:14]1)([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6]>CO>[Si:5]([O:12][C@H:13]1[CH2:17][N:16]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:25][CH:26]=2)(=[O:20])=[O:19])[C@H:15]([CH2:31][OH:32])[CH2:14]1)([C:8]([CH3:11])([CH3:9])[CH3:10])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 57659768HCID 57659768, compound

Product 1

HCID 57659753HCID 57659753, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Lithium chloride (1.21 g, 28.49 mmol) and sodium borohydride (1.08 g, 28.49 mmol) were added to a solution of (4) in (4.44 g, 9.49 mmol) in methanol (50 ml) at RT. The reaction was stirred overnight and concentrated in vacuo. The residue was dissolved in EtOAc and washed with 0.1M aqueous HCl, sat. sodium bicarbonate solution and brine. The organic layers were dried with sodium sulfate and concentrated in vacuo. The resulting crude product was purified via column chromatography using ethyl acetate/hexane gradients to yield ((2S,4R)-4-(tert-butyldimethylsilyloxy)-1-(4-(trifluoromethyl)phenylsulfonyl)pyrrolidin-2-yl)methanol (5) (2.23 g, 53%) as a white solid. MS m/z 440.2 (M+H)+; retention time=3.006 min, method [1].

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 0.1M aqueous HCl, sat. sodium bicarbonate solution and brine
  4. dry with materialThe organic layers were dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude product was purified via column chromatography

Sources & evidence

ORD record
ord-49c9307f2ab0452c94555adefbe55f71
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

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