Sodium borohydride → tert-Butyl 4-{[6-(hydroxymethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}piperidine-1-carboxylate

HRID 1426360Notes

Reaction equation

HRID 1426360 reaction equation
[CH:1]([C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=[C:5]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:4]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[N:8]=[C:7]([C:9]([F:11])([F:10])[F:12])[N:6]=[C:5]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86666511tert-Butyl 4-{[6-formyl-2-(trifluoromethyl)pyrimidin-4-yl]oxy}piperidine-1-carboxylate

Product 1

HCID 67954756tert-Butyl 4-{[6-(hydroxymethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-{[6-formyl-2-(trifluoromethyl)pyrimidin-4-yl]oxy}piperidine-1-carboxylate (202 mg, 0.538 mmol) in methanol (2.0 mL) was added sodium tetrahydroborate (20.4 mg, 0.538 mmol). The reaction solution was stirred at room temperature for 4 hours. The reaction was quenched with water and extracted with ethyl acetate (2×). The organic solutions were washed with brine, dried over Na2SC4, filtered and concentrated. The crude was purified with silica gel column to give the desired product. LCMS (M+H)+: 378.2.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate (2×)
  3. washThe organic solutions were washed with brine
  4. dry with materialdried over Na2SC4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified with silica gel column

Sources & evidence

ORD record
ord-d6a683aa0dcf49fc8724b6617e38451c
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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