Hydrochloric Acid → 2-(1-Amino-2-methyl-propyl)-6-propyl-tetrahydro-pyran-3,4,5-triol

HRID 901458Notes

Reaction equation

HRID 901458 reaction equation
[CH3:1][CH:2]([CH3:38])[CH:3]([NH2:37])[CH:4]1[CH:9]([O:10]CC2C=CC=CC=2)[CH:8]([O:18]CC2C=CC=CC=2)[CH:7]([O:26]CC2C=CC=CC=2)[CH:6]([CH2:34][CH:35]=[CH2:36])[O:5]1.Cl>C1COCC1.[Pd]>[NH2:37][CH:3]([CH:4]1[CH:9]([OH:10])[CH:8]([OH:18])[CH:7]([OH:26])[CH:6]([CH2:34][CH2:35][CH3:36])[O:5]1)[CH:2]([CH3:38])[CH3:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 692234142-Methyl-1-(6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-propylamine

Product 1

HCID 184464112-(1-Amino-2-methyl-propyl)-6-propyl-tetrahydro-pyran-3,4,5-triolYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-1-(6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-propylamine, 15c 160 mg and 100 mg degussa 50% w/w wet 10% palladium/carbon under N2 was suspended in THF (5 mL) and 1 M aq. HCl (1 mL) the reaction mixture was stirred 24 h under 1 atm pressure H2. The reaction mixture was filtered through Celite evaporated to dryness to provide the product 2-(1-Amino-2-methyl-propyl)-6-propyl-tetrahydro-pyran-3,4,5-triol (60.8 mg 89%) as the HCl salt. TLC (CHCl3: MeOH: 32% aq. AcOH)Rf=0.35. MS (ESPOS): 248 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-9b8270a6d9564bb59c1dc0d2dd61b77d
Source dataset
uspto-grants-2008_04
Patent number
US07361743B2

Reaction notes

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