Sodium borohydride → HCID 58046697, compound

HRID 2363052Notes

Reaction equation

HRID 2363052 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:8][CH2:7]2)[N:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:4][N:3]1[CH2:29][C:30]1[CH:31]=[C:32]([CH:40]=[CH:41][CH:42]=1)[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].[BH4-].[Na+]>C(O)C>[OH:22][CH:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:14][CH2:13][CH2:12][N:9]1[CH2:10][CH2:11][C:6]2([N:5]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:4][N:3]([CH2:29][C:30]3[CH:31]=[C:32]([CH:40]=[CH:41][CH:42]=3)[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:2]2=[O:1])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58046804HCID 58046804, compound

Product 1

HCID 58046697HCID 58046697, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
41 °C

Procedure

A mixture of tert-butyl 3-((4-oxo-8-(4-oxo-4-phenylbutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (1.45 g, 2.56 mmol, 1 equiv) in ethanol was warmed to 41° C. Sodium borohydride (194 mg, 5.13 mmol, 2 equiv) was slowly added and the reaction stirred as such for 30 minutes. It was stirred at room temperature for 16 h. The reaction was concentrated in vacuo and the mixture was partitioned between ethyl acetate and water, followed by a brine wash. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified using the Biotage flash chromatography system (SNAP 50 g cartridge, Rf=0.45, gradient—1%-10% methanol in dichloromethane) to afford the title compound as a cream solid (1.2 g, 83%); 1H NMR (400 MHz, DMSO-d6): δ 1.52 (s, 9H); 1.59-1.66 (m. 5H); 2.33-2.34 (m, 2H); 2.51-2.52 (m, 2H); 2.68-2.73 (m, 4H); 4.57-4.61 (m, 5H); 5.51 (d, 1H, J=3.6 Hz); 6.74-6.77 (m, 1H); 6.82 (s, 2H); 6.85 (s, 1H); 7.18-7.23 (m, 3H); 7.29-7.36 (m, 4H); 7.5-7.53 (m, 2H); 7.79 (bs, 1H); 7.82-7.84 (m, 1H); MS for C35H43N3O4 m/z 570.33 (M+H)+.

Workup

  1. stirringIt was stirred at room temperature for 16 h
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe mixture was partitioned between ethyl acetate and water
  4. washwash
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified

Sources & evidence

ORD record
ord-2e9b3bebf9ff466d9463874daff858da
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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