Hydrochloric Acid → HCID 131734369, compound

HRID 1507202Notes

Reaction equation

HRID 1507202 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH:16]2[OH:28])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:29].O1CCOCC1>C(OCC)C>[ClH:29].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:20][CH2:19][NH:18][CH2:17][C@H:16]2[OH:28])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 53401373HCID 53401373, compound

Product 1

HCID 131734369HCID 131734369, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of tert-butyl 4-(4-(benzyloxy)phenyl)-3-hydroxypiperidine-1-carboxylate (100 mg, 0.26 mmol) in 10 mL diethyl ether was added 4 M HCl in dioxane (1.3 mL, 5.2 mmol) and the resulting mixture was stirred at rt overnight. The solvent was evaporated off and the residue triturated with ether. Yield 80 mg (88%), LCMS (Method J) RT 0.73 min (92% AP), m/z 284.2 (MH+), 1H NMR (300 MHz, DMSO-d6) δ ppm 7.30-7.45 (m, 5H), 7.27 (d, J=8.4, 2H), 6.97 (d, J=8.7, 2H), 5.09 (s, 2H), 4.09 (s, 1H), 3.44 (d, J=12.6, 2H), 3.32-3.29 (m, 1H), 3.08-3.20 (m, 1H), 2.95 (d, J=12.6, 1H), 2.48-2.58 (m, 1H), 1.82 (d, J=13.2, 1H).

Workup

  1. customThe solvent was evaporated off
  2. customthe residue triturated with ether
  3. customYield 80 mg (88%), LCMS (Method J) RT 0.73 min (92% AP), m/z 284.2 (MH+), 1H NMR (300 MHz, DMSO-d6) δ ppm 7.30-7.45 (m, 5H), 7.27 (d, J=8.4, 2H), 6.97 (d, J=8.7, 2H), 5.09 (s, 2H), 4.09 (s, 1H), 3.44 (d, J=12.6, 2H), 3.32-3.29 (m, 1H), 3.08-3.20 (m, 1H), 2.95 (d, J=12.6, 1H), 2.48-2.58 (m, 1H), 1.82 (d, J=13.2, 1H)

Sources & evidence

ORD record
ord-a57b21a0313e471faa85cd1b6bfdc081
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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