Lithium borohydride → HCID 69024598, compound

HRID 878409Notes

Reaction equation

HRID 878409 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16](OC)=[O:17])[CH2:13][O:14][CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+]>CO>[OH:17][CH2:16][C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:13][O:14][CH3:15]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 69025158HCID 69025158, compound

Product 1

HCID 69024598HCID 69024598, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl N-[(benzyloxy)carbonyl]-O-methyl-L-serinate (60 g, 0.22 mol) in methanol (600 mL) was added lithium borohydride (39.2 g, 1.80 mol). After 2 hours, the reaction mixture was quenched with saturated aqueous ammonium chloride solution, partially concentrated under reduced pressure, and diluted with water. The mixture was extracted with ethyl acetate (3×100 mL), and the combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on silica gel to give benzyl [(2R)-1-hydroxy-3-methoxypropan-2-yl]carbamate. MS ESI calc'd. for C12H18NO4 [M+H]+ 240. found 240. 1H NMR (400 MHz, CDCl3) δ 7.56-7.30 (m, 5H), 5.52 (br s, 1H), 5.08 (s, 2H), 3.84 (d, J=16.0 Hz, 2H), 3.76-3.64 (m, 1H), 3.63-3.52 (m, 2H), 3.38 (s, 3H), 2.55 (bs, 1H).

Workup

  1. customthe reaction mixture was quenched with saturated aqueous ammonium chloride solution
  2. concentrationpartially concentrated under reduced pressure
  3. additiondiluted with water
  4. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified via chromatography on silica gel

Sources & evidence

ORD record
ord-61a90119371547e98ae04756baaf866f
Source dataset
uspto-grants-2015_03
Patent number
US08987456B2

Reaction notes

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