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

HRID 1908669Notes

Reaction equation

HRID 1908669 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-b14f5e76396041f9a03b5cd35c1edc6f
Source dataset
uspto-grants-2013_12
Patent number
US08598213B2

Reaction notes

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