Hydrochloric Acid → (R)-2-Amino-2-(6-propoxy-pyridin-3-yl)-ethanol

HRID 2170043Notes

Reaction equation

HRID 2170043 reaction equation
Cl.C(OCC)C.C([Si](C)(C)[O:12][CH2:13][C@H:14]([NH-:25])[C:15]1[CH:16]=[N:17][C:18]([O:21][CH2:22][CH2:23][CH3:24])=[CH:19][CH:20]=1)(C)(C)C>CO>[NH2:25][C@H:14]([C:15]1[CH:16]=[N:17][C:18]([O:21][CH2:22][CH2:23][CH3:24])=[CH:19][CH:20]=1)[CH2:13][OH:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86762171[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(6-propoxy-pyridin-3-yl)-ethyl]-amide

Product 1

HCID 86675616(R)-2-Amino-2-(6-propoxy-pyridin-3-yl)-ethanolYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2.00 M solution of hydrogen chloride in diethyl ether (28 mL, 56 mmol) was added to a stirred solution of [(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(6-propoxy-pyridin-3-yl)-ethyl]-amide (2.33 g, 5.62 mmol) dissolved in MeOH (11 mL) at 0° C. under Ar. After the addition was completed the cooling bath was removed and the solution was stirred at room temperature overnight. The mixture was then evaporated to dryness and the residue was suspended in methylene chloride and transferred to a short silica gel column. After eluding with EtOAc:EtOH:Et3N (90:5:5) (R)-2-Amino-2-(6-propoxy-pyridin-3-yl)-ethanol. IM36, was obtained as an oil (0.813 g, 74%). The overall yield from 5-bromo-2-propoxypyridine IM3 was 36%.

Workup

  1. additionAfter the addition
  2. customwas removed
  3. customThe mixture was then evaporated to dryness

Sources & evidence

ORD record
ord-a668435316b44ada8eefd31bce1ef24f
Source dataset
uspto-grants-2015_06
Patent number
US09050327B2

Reaction notes

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