Sodium borohydride → HCID 86680159, compound

HRID 1915960Notes

Reaction equation

HRID 1915960 reaction equation
NC1SC(C2C(F)=CC=CC=2F)=NC=1C(NC1C=NN(C)C=1N1CCC(C(F)F)C(N)CC1)=O.[F:35][C:36]([F:59])([F:58])[C:37]([NH:39][C@H:40]1[CH:46]([CH:47]=[O:48])[CH2:45][CH2:44][N:43]([C:49]2[N:50]([CH3:57])[N:51]=[CH:52][C:53]=2[N+:54]([O-:56])=[O:55])[CH2:42][CH2:41]1)=[O:38].[BH4-].[Na+]>CO>[F:58][C:36]([F:35])([F:59])[C:37]([NH:39][C@H:40]1[CH:46]([CH2:47][OH:48])[CH2:45][CH2:44][N:43]([C:49]2[N:50]([CH3:57])[N:51]=[CH:52][C:53]=2[N+:54]([O-:56])=[O:55])[CH2:42][CH2:41]1)=[O:38]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 74983294HCID 74983294, compoundHCID 86680158HCID 86680158, compound

Product 1

HCID 86680159HCID 86680159, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In the preparation of 511, 2,2,2-trifluoro-N-[(4R)-5-formyl-1-(2-methyl-4-nitro-pyrazol-3-yl)azepan-4-yl]acetamide (192 mg, 0.53 mmol) was dissolved in methanol (5 mL) and cooled in an ice bath. Sodium borohydride (41 mg, 1.06 mmol) was added, allowed to warm to room temperature, and stirred for 40 min. The reaction was quenched with sat. NaHCO3 and extracted with EA 3×. The combined organic layers were concentrated and the residue was purified via silica gel column chromatography (0-100% EA/heptane) to give 2,2,2-trifluoro-N-[(4R)-5-(hydroxymethyl)-1-(2-methyl-4-nitro-pyrazol-3-yl)azepan-4-yl]acetamide (120 mg, 62%).

Workup

  1. temperaturecooled in an ice bath
  2. customThe reaction was quenched with sat. NaHCO3
  3. extractionextracted with EA 3×
  4. concentrationThe combined organic layers were concentrated
  5. customthe residue was purified via silica gel column chromatography (0-100% EA/heptane)

Sources & evidence

ORD record
ord-f01fb2fc492b4b949e6b70c92400a41b
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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