Sodium borohydride → HCID 71257801, compound

HRID 2200788Notes

Reaction equation

HRID 2200788 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:12]3[N:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:15]=[C:14]([CH:22]=[O:23])[CH:13]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[BH4-].[Na+]>C(O)(C)C>[O:4]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:12]3[N:17]=[C:16]([C:18]([F:20])([F:21])[F:19])[N:15]=[C:14]([CH2:22][OH:23])[CH:13]=3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86676920HCID 86676920, compound

Product 1

HCID 71257801HCID 71257801, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

Into a 1-neck round-bottom flask, 6-(1,4-dioxaspiro[4.5]dec-8-yloxy)-2-(trifluoromethyl)pyrimidine-4-carbaldehyde (3.00 g, 9.03 mmol) was dissolved in isopropyl alcohol (40 mL) and cooled to 0° C. To this solution, NaBH4 (0.27 g, 7.2 mmol) was added, and the reaction was stirred for 5 hours until LCMS analysis of the reaction mixture showed no starting material present. The reaction was transferred to a separatory funnel and partitioned between water and EtOAc, the phases were separated and the aqueous phase was washed with EtOAc. The combined organic phase was washed with water, then saturated NaCl, dried over MgSO4 and filtered and stripped to dryness to leave the crude product. MS (ES): 335 (M+1).

Workup

  1. customThe reaction was transferred to a separatory funnel
  2. custompartitioned between water and EtOAc
  3. customthe phases were separated
  4. washthe aqueous phase was washed with EtOAc
  5. washThe combined organic phase was washed with water
  6. dry with materialsaturated NaCl, dried over MgSO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-b24df2a0489b47b6b52e1bb07c12ca48
Source dataset
uspto-grants-2016_06
Patent number
US09359358B2

Reaction notes

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