Lithium borohydride → Ether isohexane

HRID 2388766Notes

Reaction equation

HRID 2388766 reaction equation
[CH2:1]([O:3][C:4](=O)[C@H:5](OC1C=C(NS(N2CCCC2)(=O)=O)N=C(S[CH2:24][C:25]2[CH:30]=C[CH:28]=[C:27](F)[C:26]=2F)N=1)C)[CH3:2].[BH4-].[Li+]>C1COCC1>[CH3:2][CH2:1][O:3][CH2:4][CH3:5].[CH3:28][CH2:27][CH2:26][CH:25]([CH3:30])[CH3:24]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 536283522-[[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1-pyrrolidinylsulfonyl)amino]-4-pyrimidinyl]oxy]-(2R)-propanoic acid ethyl ester

Product 1

HCID 21882825Ether isohexane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound was prepared according to the procedure outlined in example 24 using a mixture of 2-[[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1-pyrrolidinylsulfonyl)amino]-4-pyrimidinyl]oxy]-(2R)-propanoic acid ethyl ester, (the product of step i) (0.38 g), THF (8 mL) and 2 M lithium borohydride in THF (1.3 mL). Purification was by reverse phase HPLC (symmetry as the stationary phase and TFA/acetonitrile as the mobile phase). The resulting oil was titurated with methanol, toluene, DCM, then ether/iso-hexane to give the title compound as a white solid. Yield: 0.15 g

Workup

  1. customThe title compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-5a0ec1440d3a48008793dd5b5053d290
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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