Sodium borohydride → HCID 86717549, compound

HRID 712097Notes

Reaction equation

HRID 712097 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:18][C@H:17]2[C@H:15]([O:16]2)[CH2:14][C@@H:13]1[C:19]([O:21][CH3:22])=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:18][C@H:17]([OH:16])[CH2:15][CH2:14][C@@H:13]1[C:19]([O:21][CH3:22])=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14320482HCID 14320482, compound

Product 1

HCID 86717549HCID 86717549, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl (1R,3S,4R,6S)-4-{[(benzyloxy)carbonyl]amino}-7-oxabicyclo[4.1.0]heptane-3-carboxylate (1.9 g, 6.2 mmol) in ethanol (30.0 mL) was added sodium tetrahydroborate (0.471 g, 12.4 mmol). The resulting mixture was stirred overnight (22 h) at room temperature. The reaction was quenched with sat. NH4Cl, then most of the solvent evaporated. The residue was taken up in EtOAc and washed with water, dried (Na2SO4), filtered and concentrated. The crude was purified on silica gel, eluted with 40-100% EtOAc in hexanes to give 0.75 g (39%) of the desired product. LCMS calculated for C16H22NO5 (M+H)+: m/z=308.1. Found: 308.0. 1H NMR (300 MHz, CDCl3) δ 7.36-7.28 (m, 5H), 6.02 (d, J=9.0 Hz, 1H), 5.05 (s, 2H), 4.03 (s, 1H), 3.87 (s, 1H), 3.64 (s, 3H), 2.68 (s, 1H), 2.22-2.11 (m, 1H), 1.97-1.67 (m, 5H), 1.42 (s, 1H) ppm.

Workup

  1. customThe reaction was quenched with sat. NH4Cl
  2. custommost of the solvent evaporated
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified on silica gel
  8. washeluted with 40-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-b97596a4e2054f0bbbaaf5cb902c59b0
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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