Hydrochloric Acid → HCID 117697489, compound

HRID 1778529Notes

Reaction equation

HRID 1778529 reaction equation
[Si]([O:8][CH:9]1[CH2:15][CH:14]2[N:16]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH:10]1[CH2:11][CH:12]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:13]2)(C(C)(C)C)(C)C.Cl>CO.O>[OH:8][CH:9]1[CH2:15][CH:14]2[N:16]([C:17]([O:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])[CH:10]1[CH2:11][CH:12]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:13]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 123932151HCID 123932151, compound

Product 1

HCID 117697489HCID 117697489, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

crude 109e was dissolved in MeOH (400 mL), 12 N HCl (40 mL, 3.0 eq) was added and then stirred at room temperature for 30 min. The mixture was diluted with water (800 mL), and extracted two times with EA (500 mL). The organic layers were combined, dried over Na2SO4 and concentrated, the residue was purified by silica gel (EA/PE=1:3) to give benzyl 6-hydroxy-3-(2-methoxy-2-oxo-ethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate 109f as a colorless oil, 30 g, yield for two steps, 70%. 1H NMR (400 MHz, DMSO-d6) δ: 7.43-7.26 (m, 5H), 5.09 (s, 2H), 4.90 (dd, J=3.6, 6.8 Hz, 1H), 4.23 (d, J=6.4 Hz, 1H), 4.16-4.09 (m, 1H), 4.12-3.92 (m, 1H), 3.59 (s, 3H), 2.38 (d, J=7.2 Hz, 2H), 2.14-1.93 (m, 5H), 1.72 (br, 1H); MS: calc'd (MH+) 334, measured (MH+) 334.

Workup

  1. extractionextracted two times with EA (500 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customthe residue was purified by silica gel (EA/PE=1:3)

Sources & evidence

ORD record
ord-bd130093d6d74874857ae1108b69be90
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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