Hydrochloric Acid → 2-Benzyl-2,5-diazaspiro[3.4]octane--hydrogen chloride (1/2)

HRID 1842711Notes

Reaction equation

HRID 1842711 reaction equation
[ClH:1].[CH2:2]([N:9]1[CH2:12][C:11]2([CH2:16][CH2:15][CH2:14][N:13]2C(OC(C)(C)C)=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CCOC(C)=O>[ClH:1].[ClH:1].[CH2:2]([N:9]1[CH2:12][C:11]2([CH2:16][CH2:15][CH2:14][NH:13]2)[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 712394042,5-Diazaspiro[3.4]octane-5-carboxylic acid, 2-(phenylmethyl)-, 1,1-dimethylethyl ester2×

Product 1

HCID 509990282-Benzyl-2,5-diazaspiro[3.4]octane--hydrogen chloride (1/2)Yield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A 4M solution of HCl in EtOAc (2 L) was added to a solution of tert-butyl 2-benzyl-2,5-diazaspiro[3.4]octane-5-carboxylate (Intermediate 50, 195 g, 644.8 mmol) in EtOAc (0.5 L) and the mixture was stirred for 12 h. The resulting solid was collected by filtration and washed with tert-butylmethyl ether (2 L) to give the title salt (170 g, 96%) as white solid; 1H NMR: (d4-methanol) 2.04-2.11 (2H, m), 2.41 (2H, t), 3.39 (2H, t), 4.33 (2H, s), 4.81-4.88 (2H, m), 7.49-7.58 (5H, m).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with tert-butylmethyl ether (2 L)

Sources & evidence

ORD record
ord-1c5d113fcfb14374890cdabe5fbaf436
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

Loading…