Methanol → ((2S,5R)-5-Aminotetrahydro-2H-pyran-2-yl)methanol

HRID 470691Notes

Reaction equation

HRID 470691 reaction equation
ClC1N=C2NC(=O)C3([C@@H](C4C=CC=C(Cl)C=4F)[C@H](C(N[C@H]4CC[C@H](CO)CC4)=O)[N:12]([C@H:34]([C:43]4[CH:48]=[CH:47][CH:46]=CC=4)[C@@H:35]([OH:42])C4C=CC=CC=4)C43CCC(C)(C)CC4)C2=CC=1.[H][H].C[OH:60]>[C].[Pd]>[NH2:12][C@@H:34]1[CH2:43][CH2:48][C@@H:47]([CH2:46][OH:60])[O:42][CH2:35]1

Participants

5

Reactant 3

HCID 887MethanolHCID 178418361HCID 178418361, compoundHCID 178423624HCID 178423624, compound

Product 1

HCID 68309391((2S,5R)-5-Aminotetrahydro-2H-pyran-2-yl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

The compound (2.00 g, 7.54 mmol) obtained in Step 2 above was dissolved in methanol (30 ml), 10% palladium carbon (300 mg) was added and the resulting mixture was stirred at room temperature for 4 hours in a hydrogen atmosphere. The catalyst was removed by filtration through celite and then the filtrate was concentrated under reduced pressure and dried to give 1.13 g (100%) of the title compound as a colorless solid.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customdried

Sources & evidence

ORD record
ord-16734a80ba4f45e094f5343a8084f11d
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

Loading…