Sodium borohydride → (S)-Methyl 2-(4-(hydroxymethyl)-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoate

HRID 1513206Notes

Reaction equation

HRID 1513206 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([O:10][C@@H:11]([C:16]([O:29][CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[N:4]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([O:10][C@@H:11]([C:16]([O:29][CH3:30])([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12]([O:14][CH3:15])=[O:13])[N:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59441456(S)-Methyl 2-(4-formyl-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoate

Product 1

HCID 59441450(S)-Methyl 2-(4-(hydroxymethyl)-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoateYield 8.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the crude compound from Example 10 (76 mmol) in methanol (170 mL) is added sodium borohydride (1.93 g, 51 mmol) portion-wise and the reaction stirred for 3 hr. The reaction is quenched with ice-water (50 mL) and the methanol is removed under reduced pressure on a rotary evaporator. The residual aqueous phase is extracted with ethyl acetate (2×100 mL) to yield crude product (25 g). This crude product is purified by column chromatography on silica gel eluted with ethyl acetate/hexane to yield the title compound (1.8 g, 8.6%). MS m/z 409.1 (M+.+1).

Workup

  1. customThe reaction is quenched with ice-water (50 mL)
  2. customthe methanol is removed under reduced pressure on a rotary evaporator
  3. extractionThe residual aqueous phase is extracted with ethyl acetate (2×100 mL)
  4. customto yield crude product (25 g)
  5. customThis crude product is purified by column chromatography on silica gel
  6. washeluted with ethyl acetate/hexane

Sources & evidence

ORD record
ord-15b117a0bb4849e2b4a62fb982d391a1
Source dataset
uspto-grants-2012_07
Patent number
US08217155B2

Reaction notes

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