Sodium borohydride → HCID 59159296, compound

HRID 1096259Notes

Reaction equation

HRID 1096259 reaction equation
[BH4-].[Na+].C[O:4][C:5](=O)[CH:6]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[CH:20]([CH3:34])[C:19]1=[O:35])[CH2:7][CH2:8][N:9]1[CH2:16][CH2:15][C:12]2([CH2:14][CH2:13]2)[C@H:11]([OH:17])[CH2:10]1>CCO>[OH:17][C@@H:11]1[CH2:10][N:9]([CH2:8][CH2:7][CH:6]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:33])[F:31])[CH:25]=3)[CH:20]([CH3:34])[C:19]2=[O:35])[CH2:5][OH:4])[CH2:16][CH2:15][C:12]21[CH2:13][CH2:14]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59159268HCID 59159268, compound

Product 1

HCID 59159296HCID 59159296, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (63 mg, 1.7 mmol) was added at RT to a solution of 4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-2-[3-methyl-2-oxo-4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-butyric acid methyl ester (example 54; 80 mg, 0.17 mmol) in EtOH (2 mL). The reaction mixture was heated at reflux for 2 h, then after cooling partitioned between CH2Cl2 and 10% aq. KHSO4 solution. The organic layer was dried (MgSO4), filtered, and evaporated. Chromatography (IST Isolute® Flash NH2; EtOAc/MeOH 19:1) afforded the title compound (42 mg, 56%). Colorless oil, MS: 456.3 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. temperatureafter cooling
  4. custompartitioned between CH2Cl2 and 10% aq. KHSO4 solution
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c2e9667144844785b43db89851927f60
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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