Sodium borohydride → HCID 86597689, compound

HRID 547787Notes

Reaction equation

HRID 547787 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:46])([F:45])[C:5]1[CH:6]=[C:7]([C:15]([CH3:44])([CH3:43])[C:16]([N:18]([C:20]2[CH:21]=[N:22][C:23]([N:35]3[CH2:39][C@H:38]([OH:40])[CH2:37][C@H:36]3[CH2:41][OH:42])=[CH:24][C:25]=2[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=2[CH:33]=[O:34])[CH3:19])=[O:17])[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1>CO>[F:45][C:4]([F:3])([F:46])[C:5]1[CH:6]=[C:7]([C:15]([CH3:44])([CH3:43])[C:16]([N:18]([C:20]2[CH:21]=[N:22][C:23]([N:35]3[CH2:39][C@H:38]([OH:40])[CH2:37][C@H:36]3[CH2:41][OH:42])=[CH:24][C:25]=2[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=2[CH2:33][OH:34])[CH3:19])=[O:17])[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86597690HCID 86597690, compound

Product 1

HCID 86597689HCID 86597689, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 24 mg (0.637 mmol) sodium borohydride in 1 ml methanol were added 100 mg (0.159 mmol) (2S,4R)-2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(4-fluoro-2-formyl-phenyl)-6-(4-hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-pyridin-3-yl]-N-methyl-isobutyramide at room temperature. After stirring for 1 h the reaction mixture was concentrated in vacuo and partitioned between ethyl acetate and saturated sodium carbonate solution. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography to give 78 mg (78%) of the title compound as a white foam.

Workup

  1. concentrationwas concentrated in vacuo
  2. custompartitioned between ethyl acetate and saturated sodium carbonate solution
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-2fa929fc3ded42d495244cb330fd9010
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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