Tetrahydrofuran → HCID 68686380, compound

HRID 638958Notes

Reaction equation

HRID 638958 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][N:8]([CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:9][C:10](=[O:13])[CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:27])[CH2:7][N:8]([CH:14]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:9][CH:10]([OH:13])[CH2:11][CH3:12])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 68685786HCID 68685786, compound

Product 1

HCID 68686380HCID 68686380, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of [benzhydryl-(2-oxobutyl)amino]acetic acid tert-butyl ester (7.4 g, 20.1 mmol, 1 eq.) in dry MeOH:THF (100 mL, 1:1) at −23° C., was added CeCl3.7H2O (1.43 g, 3.83 mmol, 0.19 eq.). The reaction mixture was stirred until homogeneous, then NaBH4 (0.57 g, 15.1 mmol, 0.75 eq.) was added slowly (in small portions). The reaction was stirred for additional 20 min, then poured onto brine. This mixture was extracted with DCM, dried over MgSO4, filtered, and concentrated in vacuo to afford [benzhydryl-(2-hydroxybutyl)amino]acetic acid tert-butyl ester in quantative yield. This was used without further purification. ESMS: m/z 370.4 [M+H].

Workup

  1. additionwas added slowly (in small portions)
  2. additionpoured onto brine
  3. extractionThis mixture was extracted with DCM
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c1414e1891242bfb18ed17bee562026
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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