Water → HCID 53246036, compound

HRID 527501Notes

Reaction equation

HRID 527501 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:42])[N:10]([C@H:13]2[C@H:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[CH2:16][N:15]([C:25]([CH:27]3[CH2:32][CH2:31][N:30]([C:33]4[CH:38]=[CH:37][C:36]([C:39](=[O:41])[CH3:40])=[CH:35][N:34]=4)[CH2:29][CH2:28]3)=[O:26])[CH2:14]2)[CH2:11][CH3:12])=[CH:4][CH:3]=1.[BH4-].[Na+].O>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:42])[N:10]([C@H:13]2[C@H:17]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[CH2:16][N:15]([C:25]([CH:27]3[CH2:32][CH2:31][N:30]([C:33]4[CH:38]=[CH:37][C:36]([CH:39]([OH:41])[CH3:40])=[CH:35][N:34]=4)[CH2:29][CH2:28]3)=[O:26])[CH2:14]2)[CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 53247602HCID 53247602, compound

Product 1

HCID 53246036HCID 53246036, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 62 mg (0.15 mmol) [(3S,4R)-1-(5′-Acetyl-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4-carbonyl)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-ethyl-carbamic acid 4-fluoro-phenyl ester (example 14) and 3.95 mg (0.105 mmol) sodium borohydride in 2 mL THF/0.2 mL MeOH was stirred at room temperature for 45 minutes. Water was added and the mixture was extracted with ethyl acetate. The combined organic layers were dried with Na2SO4, filtered and evaporated to dryness to yield 58 mg (93%) of the title compound as off-white solid. MS m/e: 595.2 [M+H]+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried with Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-71c6680610aa47abb35f9776f0dd56fd
Source dataset
uspto-grants-2016_05
Patent number
US09346786B2

Reaction notes

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