Hydrochloric Acid → HCID 70346867, compound

HRID 1420307Notes

Reaction equation

HRID 1420307 reaction equation
CC(OC(=O)[NH:7][C@H:8]([CH2:16][OH:17])[CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)(C)C.[ClH:19]>O1CCOCC1>[ClH:19].[ClH:19].[NH2:7][C@@H:8]([CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:16][OH:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 105869181,1-Dimethylethyl N-[(1S)-1-(hydroxymethyl)-2-(3-pyridinyl)ethyl]carbamate

Product 1

HCID 70346867HCID 70346867, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

To a solution of (S)-[1-(hydroxymethyl)-2-(3-pyridinyl)ethyl]carbamic acid 1,1-dimethylethyl ester (1.27 g, 5.03 mmol) in 1,4-dioxan (3 ml) was added 1,4-dioxan saturated with HCl gas (10 ml) followed by a further portion of 1,4-dioxan (10 ml). After 2 h at room temperature the precipitated solid was collected by filtration, washed with 1,4-dioxan (5 ml) and ether then dried in vacuo to give the title compound (0.928 g) as a solid, nmr(δ,DMSO-d6) includes 3.11(bd,2H), 3.4-3.7(m,3H), 7.86(dd,1H), 8.1-8.3(bs,3H), 8.45(d,1H), 8.81(d,1H), 8.9(s,1H).

Workup

  1. filtrationAfter 2 h at room temperature the precipitated solid was collected by filtration
  2. washwashed with 1,4-dioxan (5 ml) and ether
  3. customthen dried in vacuo

Sources & evidence

ORD record
ord-04cfa7941e7346bc92f4450c5733ffc9
Source dataset
uspto-grants-1999_03
Patent number
US05889178

Reaction notes

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