Dichloromethane → HCID 45100810, compound

HRID 1096257Notes

Reaction equation

HRID 1096257 reaction equation
[BH4-].[Na+].C[O:4][C:5](=[O:37])[CH:6]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:34])([F:33])[F:32])[CH:25]=2)[CH:20]([CH3:35])[C:19]1=[O:36])[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.OS([O-])(=O)=O.[K+].C(Cl)Cl>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]([O:30][C:31]([F:34])([F:33])[F:32])[CH:25]=3)[CH:20]([CH3:35])[C:19]2=[O:36])[C:5]([OH:37])=[O:4])[CH2:16][CH2:15][C:12]21[CH2:14][CH2:13]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516920Potassium bisulfateHCID 4311764Sodium borohydride3×HCID 59159258HCID 59159258, compound

Product 1

HCID 45100810HCID 45100810, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Sodium borohydride (11 mg, 0.28 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-trifluoromethoxy-phenyl)-piperazin-1-yl]-butyric acid methyl ester (70 mg, 0.14 mmol) in EtOH (2 mL), then after 16 min another portion of sodium borohydride (11 mg, 0.28 mmol) was added. After 24 h another portion of sodium borohydride (30 mg, 0.80 mmol) was added and the reaction mixture heated at 60° C. for 6 h. After cooling 10% aq. KHSO4 solution and CH2Cl2 were added to the reaction mixture, the organic layer washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; CH2Cl2/MeOH 4:1, then CH2Cl2/MeOH/25% aq. ammonia solution 80:20:1) afforded 4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-2-[3-methyl-2-oxo-4-(3-trifluoromethoxy-phenyl)-piperazin-1-yl]-butyric acid (41 mg, 60%; light yellow solid, MS: 484.2 (M−H)−) and 1-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-1-hydroxymethyl-propyl]-3-methyl-4-(3-trifluoromethoxy-phenyl)-piperazin-2-one (22 mg, 33%; colorless oil, MS: 472.2 (M+H)+).

Workup

  1. additionwere added to the reaction mixture
  2. washthe organic layer washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-bc8a3063e2f848b9897f3fcd1aa2a514
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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