Aluminium lithium hydride → HCID 86696667, compound

HRID 1774169Notes

Reaction equation

HRID 1774169 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([NH:14][C@H:15]1[CH2:20][CH2:19][O:18][C@@H:17]([C:21](OCC)=[O:22])[CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([NH:14][C@H:15]1[CH2:20][CH2:19][O:18][C@@H:17]([CH2:21][OH:22])[CH2:16]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 131731317HCID 131731317, compound

Product 1

HCID 86696667HCID 86696667, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (1.0 g, 26 mol) was added at 0° C. to a stirred solution of cis-ethyl 4-(benzylamino)-tetrahydro-2H-pyran-2-carboxylate (1.3 g, 5.0 mol) in anhydrous THF (50 mL) After stirring for 1 hour, the reaction was quenched by slow, sequential addition of water (1 mL), 15% NaOH (1 mL), and water (3 mL). The inorganic salt was filtered off, and the filtrated was diluted with EtOAc (50 mL), dried and concentrated to give cis-4-(benzylamino)-(tetrahydro-2H-pyran-2-yl)methanol (1.1 g, 100% yield). LCMS (ESI) m/z: 222.3 [M+H]+.

Workup

  1. customthe reaction was quenched by slow,
  2. additionsequential addition of water (1 mL), 15% NaOH (1 mL), and water (3 mL)
  3. filtrationThe inorganic salt was filtered off
  4. additionthe filtrated was diluted with EtOAc (50 mL)
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c6c2d24dcc354b38a53a05fafc1ffd90
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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