Sodium triacetoxyborohydride → (4R)-methyl 3-methyl-4-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-3-carboxylate

HRID 736781Notes

Reaction equation

HRID 736781 reaction equation
[CH3:1][C:2]1([C:17]([O:19][CH3:20])=[O:18])[C:7](=[N:8][C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH2:6][CH2:5][O:4][CH2:3]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(#N)C.C(O)(=O)C>[CH3:1][C:2]1([C:17]([O:19][CH3:20])=[O:18])[C@H:7]([NH:8][C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH2:6][CH2:5][O:4][CH2:3]1

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 68817214Methyl 3-methyl-4-((R)-1-phenylethylimino)-tetrahydro-2H-pyran-3-carboxylate

Product 1

HCID 68821088(4R)-methyl 3-methyl-4-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-3-carboxylateYield 37%

Reagents, catalysts & solvents 1

HCID 22391770Acetonitrile aceticacidSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3-methyl-4-((R)-1-phenylethylimino)-tetrahydro-2H-pyran-3-carboxylate (crude, 13.53 mmol) in acetonitrile-acetic acid (1:1, 80 mL) was treated with NaBH(OAc)3 and stirred for 2.5 h at 0° C. Following concentration in vacuo, the residue was dissolved in ethyl acetate (200 mL), washed with saturated NaHCO3 until the aqueous phase was basic, dried over MgSO4, and purified by chromatography with 20% ethyl acetate/hexane to yield 1.37 g (37% in 2 steps) of (4R)-methyl 3-methyl-4-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-3-carboxylate. MS: (M+H)+=278.1.

Workup

  1. concentrationconcentration in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  3. washwashed with saturated NaHCO3 until the aqueous phase
  4. dry with materialdried over MgSO4
  5. custompurified by chromatography with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-161aeb6776734943aef6828f9a26e91b
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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